JP2004140342A - Composite insulating film - Google Patents
Composite insulating film Download PDFInfo
- Publication number
- JP2004140342A JP2004140342A JP2003317572A JP2003317572A JP2004140342A JP 2004140342 A JP2004140342 A JP 2004140342A JP 2003317572 A JP2003317572 A JP 2003317572A JP 2003317572 A JP2003317572 A JP 2003317572A JP 2004140342 A JP2004140342 A JP 2004140342A
- Authority
- JP
- Japan
- Prior art keywords
- group
- insulating film
- atom
- film
- butoxysilane
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000002131 composite material Substances 0.000 title claims abstract description 42
- BGECDVWSWDRFSP-UHFFFAOYSA-N borazine Chemical compound B1NBNBN1 BGECDVWSWDRFSP-UHFFFAOYSA-N 0.000 claims abstract description 41
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims abstract description 32
- 239000011347 resin Substances 0.000 claims abstract description 27
- 229920005989 resin Polymers 0.000 claims abstract description 27
- 229910052710 silicon Inorganic materials 0.000 claims abstract description 15
- 238000000576 coating method Methods 0.000 claims description 43
- 239000011248 coating agent Substances 0.000 claims description 40
- 125000003118 aryl group Chemical group 0.000 claims description 28
- 150000001875 compounds Chemical class 0.000 claims description 27
- -1 poly (dimethylsiloxy) group Chemical group 0.000 claims description 26
- 125000004432 carbon atom Chemical group C* 0.000 claims description 24
- 239000011342 resin composition Substances 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 20
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 19
- 125000004429 atom Chemical group 0.000 claims description 17
- 230000003301 hydrolyzing effect Effects 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 125000000962 organic group Chemical group 0.000 claims description 3
- 125000004437 phosphorous atom Chemical group 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 abstract description 37
- 239000002184 metal Substances 0.000 abstract description 37
- 238000000034 method Methods 0.000 abstract description 16
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 abstract description 12
- 239000010703 silicon Substances 0.000 abstract description 12
- 238000004528 spin coating Methods 0.000 abstract description 9
- 230000001070 adhesive effect Effects 0.000 abstract description 2
- 239000002904 solvent Substances 0.000 description 33
- 239000010410 layer Substances 0.000 description 28
- 239000003054 catalyst Substances 0.000 description 24
- 229920000642 polymer Polymers 0.000 description 23
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 22
- 229910052757 nitrogen Inorganic materials 0.000 description 21
- 238000006116 polymerization reaction Methods 0.000 description 18
- 239000000243 solution Substances 0.000 description 18
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- 229910052697 platinum Inorganic materials 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical group C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 8
- 239000011229 interlayer Substances 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 239000011148 porous material Substances 0.000 description 8
- 239000004065 semiconductor Substances 0.000 description 8
- 239000000758 substrate Substances 0.000 description 8
- 235000012431 wafers Nutrition 0.000 description 8
- 125000003545 alkoxy group Chemical group 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000003990 capacitor Substances 0.000 description 6
- 229920001577 copolymer Polymers 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 238000005227 gel permeation chromatography Methods 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000002994 raw material Substances 0.000 description 6
- LDMRLRNXHLPZJN-UHFFFAOYSA-N 3-propoxypropan-1-ol Chemical compound CCCOCCCO LDMRLRNXHLPZJN-UHFFFAOYSA-N 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 5
- 238000006482 condensation reaction Methods 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 230000007062 hydrolysis Effects 0.000 description 5
- 238000006460 hydrolysis reaction Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
- WZJUBBHODHNQPW-UHFFFAOYSA-N 2,4,6,8-tetramethyl-1,3,5,7,2$l^{3},4$l^{3},6$l^{3},8$l^{3}-tetraoxatetrasilocane Chemical compound C[Si]1O[Si](C)O[Si](C)O[Si](C)O1 WZJUBBHODHNQPW-UHFFFAOYSA-N 0.000 description 4
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 4
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 4
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- 239000004793 Polystyrene Substances 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 125000006267 biphenyl group Chemical group 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 4
- 238000004817 gas chromatography Methods 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000011810 insulating material Substances 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 125000001624 naphthyl group Chemical group 0.000 description 4
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- PGMYKACGEOXYJE-UHFFFAOYSA-N pentyl acetate Chemical compound CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 description 4
- 238000005498 polishing Methods 0.000 description 4
- 229920002223 polystyrene Polymers 0.000 description 4
- ODLMAHJVESYWTB-UHFFFAOYSA-N propylbenzene Chemical compound CCCC1=CC=CC=C1 ODLMAHJVESYWTB-UHFFFAOYSA-N 0.000 description 4
- 239000010453 quartz Substances 0.000 description 4
- 239000002516 radical scavenger Substances 0.000 description 4
- 239000000377 silicon dioxide Substances 0.000 description 4
- 238000003860 storage Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 3
- 239000007983 Tris buffer Substances 0.000 description 3
- 125000000732 arylene group Chemical group 0.000 description 3
- DSVRVHYFPPQFTI-UHFFFAOYSA-N bis(ethenyl)-methyl-trimethylsilyloxysilane;platinum Chemical compound [Pt].C[Si](C)(C)O[Si](C)(C=C)C=C DSVRVHYFPPQFTI-UHFFFAOYSA-N 0.000 description 3
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 3
- 238000005229 chemical vapour deposition Methods 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000001723 curing Methods 0.000 description 3
- 238000009792 diffusion process Methods 0.000 description 3
- 239000004210 ether based solvent Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 229910017604 nitric acid Inorganic materials 0.000 description 3
- 229920001296 polysiloxane Polymers 0.000 description 3
- 229910052703 rhodium Inorganic materials 0.000 description 3
- 239000010948 rhodium Substances 0.000 description 3
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- UHXCHUWSQRLZJS-UHFFFAOYSA-N (4-dimethylsilylidenecyclohexa-2,5-dien-1-ylidene)-dimethylsilane Chemical compound C[Si](C)C1=CC=C([Si](C)C)C=C1 UHXCHUWSQRLZJS-UHFFFAOYSA-N 0.000 description 2
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 description 2
- QEGNUYASOUJEHD-UHFFFAOYSA-N 1,1-dimethylcyclohexane Chemical compound CC1(C)CCCCC1 QEGNUYASOUJEHD-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 description 2
- OJVAMHKKJGICOG-UHFFFAOYSA-N 2,5-hexanedione Chemical compound CC(=O)CCC(C)=O OJVAMHKKJGICOG-UHFFFAOYSA-N 0.000 description 2
- PTTPXKJBFFKCEK-UHFFFAOYSA-N 2-Methyl-4-heptanone Chemical compound CC(C)CC(=O)CC(C)C PTTPXKJBFFKCEK-UHFFFAOYSA-N 0.000 description 2
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 2
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
- QPRQEDXDYOZYLA-UHFFFAOYSA-N 2-methylbutan-1-ol Chemical compound CCC(C)CO QPRQEDXDYOZYLA-UHFFFAOYSA-N 0.000 description 2
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- YBGLWNXXCNGDQK-UHFFFAOYSA-N C(#CC)CN1BN(BN(B1)C)C Chemical compound C(#CC)CN1BN(BN(B1)C)C YBGLWNXXCNGDQK-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- LTEQMZWBSYACLV-UHFFFAOYSA-N Hexylbenzene Chemical compound CCCCCCC1=CC=CC=C1 LTEQMZWBSYACLV-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
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- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 229910004298 SiO 2 Inorganic materials 0.000 description 2
- 229910020177 SiOF Inorganic materials 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000003377 acid catalyst Substances 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- QUKGYYKBILRGFE-UHFFFAOYSA-N benzyl acetate Chemical compound CC(=O)OCC1=CC=CC=C1 QUKGYYKBILRGFE-UHFFFAOYSA-N 0.000 description 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
- 238000011088 calibration curve Methods 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000002485 combustion reaction Methods 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
- 230000032798 delamination Effects 0.000 description 2
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 2
- 229940019778 diethylene glycol diethyl ether Drugs 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000003759 ester based solvent Substances 0.000 description 2
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 2
- XLLIQLLCWZCATF-UHFFFAOYSA-N ethylene glycol monomethyl ether acetate Natural products COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- GAEKPEKOJKCEMS-UHFFFAOYSA-N gamma-valerolactone Chemical compound CC1CCC(=O)O1 GAEKPEKOJKCEMS-UHFFFAOYSA-N 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
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Images
Abstract
Description
本発明は、複合絶縁被膜び電子部品に関する。 The present invention relates to a composite insulating film and an electronic component.
LSI等の半導体素子といった電子部品(デバイス)の高集積化による配線の微細化に伴い、配線間容量の増大による信号遅延時間の増大が問題となっており、電子部品の絶縁材料に対して、耐熱性、機械特性等の他、更なる低比誘電率と熱処理工程の短縮が求められている。 With the miniaturization of wiring due to the high integration of electronic components (devices) such as semiconductor elements such as LSIs, an increase in signal delay time due to an increase in capacitance between wirings has become a problem. In addition to heat resistance, mechanical properties, etc., further low relative dielectric constant and shortening of the heat treatment process are required.
一般に配線の信号伝搬速度(v)と、配線材料が接する絶縁材料の比誘電率(ε)とは、v=k/√ε(kは定数)で表される関係を有している。つまり、使用する周波数領域を高くすると共に、絶縁材料の比誘電率(ε)を低減することにより、信号伝搬の高速化が達成される。例えば、従来から、比誘電率が4.2程度のCVD法によって形成されるSiO2膜が層間絶縁膜の形成材料として用いられてきたが、デバイスの配線間容量を低減し、LSIの動作速度を向上させる観点から、更なる低誘電率を発現する材料が切望されている。 In general, the signal propagation speed (v) of a wiring and the relative dielectric constant (ε) of an insulating material with which a wiring material is in contact have a relationship represented by v = k / √ε (k is a constant). That is, by increasing the frequency range to be used and reducing the relative dielectric constant (ε) of the insulating material, high speed signal propagation is achieved. For example, conventionally, an SiO 2 film formed by a CVD method having a relative dielectric constant of about 4.2 has been used as a material for forming an interlayer insulating film. From the viewpoint of improving the quality, a material that further develops a low dielectric constant has been desired.
これに対し、現在実用化されている低誘電率材料としては、比誘電率が3.5程度のCVD法で形成されるSiOF膜が挙げられる。また、比誘電率が2.6〜3.0である絶
縁材料としては、有機SOG(Spin On Glass)、有機ポリマー等を例示できる。さらに、比誘電率が2.6以下の絶縁材料としては、膜中に空隙を有するポーラス材が有力と考えられており、LSIの層間絶縁膜に適用するための検討・開発が盛んに行われている。
On the other hand, as a low dielectric constant material that is currently put into practical use, there is an SiOF film formed by a CVD method having a relative dielectric constant of about 3.5. Further, examples of the insulating material having a relative dielectric constant of 2.6 to 3.0 include an organic SOG (Spin On Glass), an organic polymer, and the like. Further, as an insulating material having a relative dielectric constant of 2.6 or less, a porous material having voids in the film is considered to be effective, and studies and developments for application to an interlayer insulating film of an LSI are actively conducted. ing.
そのようなポーラス材の形成方法として、金属アルコキシシランの加水分解縮重合物と共に加熱することにより揮発又は分解する特性を有するポリマーを含む組成物から被膜を形成し、この被膜を加熱することによって空孔を形成することにより絶縁被膜を形成する方法が提案されている(例えば、特許文献1及び2参照。)。
しかし、上記従来のポーラス化によって低誘電率化が達成される絶縁被膜は、低誘電率化が助長されるにつれて膜強度の低下を伴う傾向にあり、例えばCMP等により膜の平坦化を行う際に、膜の剥がれといった不都合が生じ易くなってしまい、プロセス応性や、かかる絶縁被膜を用いたデバイスの信頼性が低下してしまうといった大きな問題があった。 However, the above-mentioned insulating film, which achieves a low dielectric constant by making it porous, tends to have a decrease in film strength as the low dielectric constant is promoted. For example, when the film is planarized by CMP or the like, In addition, problems such as peeling of the film are likely to occur, and there is a serious problem that process responsiveness and reliability of a device using such an insulating film are reduced.
また、LSIの層間絶縁被膜に適用する材料には、低誘電率の他に優れた耐熱性及び高接着性が要求される。極微細化した次世代LSIの多層配線工程においては、グローバル平坦化のため、CMP(Chemical Mechanical Polishing)が必須であり、かかるCMPにおける耐研磨性を高めるため接着性は特に重要なファクターとなる。 (4) In addition to the low dielectric constant, the material applied to the interlayer insulating film of the LSI is required to have excellent heat resistance and high adhesiveness. In the multilayer wiring process of the next-generation LSI that has been miniaturized, CMP (Chemical Mechanical Polishing) is indispensable for global flattening, and adhesion is a particularly important factor in order to improve the polishing resistance in such CMP.
これに対し、比誘電率3.0以下の低誘電率材料として有力と考えられている先述した有機SOG、有機ポリマー及びポーラス材等は、従来のCVDで形成したSiO2膜やSiOF膜に比して誘電率が低いものの、配線形成におけるトレンチ(溝)加工に必要なハードマスクといった上層膜に対する接着性が十分ではない傾向にある。このため、CMP工程において、これらの低誘電率材料で構成される絶縁被膜と上層膜との間で剥離が生じ易いことが問題となっており、低誘電率材料の接着性の改善が強く望まれている。 On the other hand, the above-mentioned organic SOG, organic polymer, porous material, and the like, which are considered to be effective as low dielectric constant materials having a relative dielectric constant of 3.0 or less, have a higher dielectric constant than SiO 2 films and SiOF films formed by conventional CVD. Although the dielectric constant is low, the adhesiveness to an upper layer film such as a hard mask required for processing a trench in forming a wiring tends to be insufficient. For this reason, in the CMP process, there is a problem that peeling easily occurs between the insulating film composed of these low dielectric constant materials and the upper layer film, and it is strongly desired to improve the adhesiveness of the low dielectric constant material. It is rare.
そこで、本発明はかかる事情に鑑みてなされたものであり、十分な低誘電率化が可能であり、しかも機械強度を高めることができ且つ上層膜との接着性を向上できる複合絶縁被膜及びそれを用いた電子部品を提供することを目的とする。 Accordingly, the present invention has been made in view of the above circumstances, and a composite insulating film capable of sufficiently lowering the dielectric constant, improving mechanical strength, and improving adhesiveness to an upper film, and a composite insulating film therefor. It is an object of the present invention to provide an electronic component using the same.
上記課題を解決するために、本発明者による複合絶縁被膜は、シロキサン樹脂(ポリシロキサン)を含有して成る第1の絶縁被膜と、第1の絶縁被膜上に形成されており且つ分子構造中にボラジン骨格を有する化合物を含有して成る第2の絶縁被膜とを備えるものである。 In order to solve the above-mentioned problems, a composite insulating film of the present inventor is provided with a first insulating film containing a siloxane resin (polysiloxane), a first insulating film formed on the first insulating film, and having a molecular structure. And a second insulating coating containing a compound having a borazine skeleton.
このような構成を有する複合絶縁被膜においては、第1の絶縁被膜がシロキサン樹脂を含むので、その原料液から樹脂形成を行う際に被膜中に空孔を導入し易く、ポーラス化による低誘電率化が可能である。また、その上に形成される第2の絶縁被膜が分子構造中にボラジン骨格を含むので当該被膜の低誘電率化ひいては複合絶縁被膜全体の更なる低誘電率化が達成される。また、第2の絶縁被膜の誘電率を第1の絶縁被膜に比して小さくすることができるので、第1の絶縁被膜のポーラス化を過度に促進させなくともよい。よって、第1の絶縁被膜ひいては複合絶縁被膜全体の機械強度を高めることができる。 In the composite insulating coating having such a configuration, since the first insulating coating contains a siloxane resin, holes are easily introduced into the coating when the resin is formed from the raw material liquid, and a low dielectric constant due to a porous structure is obtained. Is possible. Further, since the second insulating film formed thereon includes a borazine skeleton in the molecular structure, the dielectric constant of the film is further reduced, and the dielectric constant of the entire composite insulating film is further reduced. Further, since the dielectric constant of the second insulating coating can be made smaller than that of the first insulating coating, it is not necessary to excessively promote the formation of the porous first insulating coating. Therefore, the mechanical strength of the first insulating coating and thus the entire composite insulating coating can be increased.
さらに、ボラジン含有ケイ素ポリマー層等で構成される第2の絶縁被膜は、他層への被着能、換言すれば他層との接着能に極めて優れたものである。本発明の複合絶縁被膜では、かかる高接着特性を発現する第2の絶縁被膜が第1の絶縁被膜の上に設けられているので、複合絶縁被膜上にハードマスク等の上層膜が形成される場合、その上層膜は第2の絶縁被膜に被着され、両者の固着が強固なものとなる。また、同様にして第1の絶縁被膜と第2の絶縁被膜との固着も強化される。したがって、複合絶縁被膜の内部及び複合絶縁被膜と上層膜との接着性が高められ、CMP等において層剥離が生じることが防止される。 {Circle around (2)} The second insulating film composed of the borazine-containing silicon polymer layer and the like has extremely excellent adhesion to other layers, in other words, excellent adhesion to other layers. In the composite insulating coating of the present invention, since the second insulating coating exhibiting such high adhesive properties is provided on the first insulating coating, an upper layer film such as a hard mask is formed on the composite insulating coating. In this case, the upper layer film is applied to the second insulating film, so that the two are firmly fixed. Similarly, the adhesion between the first insulating film and the second insulating film is also strengthened. Therefore, the adhesiveness between the inside of the composite insulating coating and the upper insulating film and between the composite insulating coating and the upper layer film is improved, and the occurrence of delamination during CMP or the like is prevented.
具体的には、第1の絶縁被膜が、下記式(1); Specifically, the first insulating film has the following formula (1);
X1 nSiX2 4-n …(1)、
で表される化合物を加水分解縮合して得られるシロキサン樹脂を含むシロキサン樹脂組成物から成るものであると好ましい。式中、X1は、H原子若しくはF原子、又はB原子、N原子、Al原子、P原子、Si原子、Ge原子若しくはTi原子を含む基、又は炭素数1〜20の有機基を示し、X2は加水分解性基を示し、nは0〜2の整数を示し、nが2のとき、各X1は同一でも異なっていてもよく、nが0〜2のとき、各X2は同一でも異なっていてもよい。
X 1 n SiX 2 4-n (1),
And a siloxane resin composition containing a siloxane resin obtained by hydrolyzing and condensing the compound represented by the formula (1). In the formula,
こうすれば、第1の絶縁被膜の原材料として、式(1)で表される化合物を溶媒(溶剤)に溶解させて成る液とし易く、これを塗布した後、加熱により加水分解縮合を生ぜしめてシロキサン樹脂を生成すると共に硬化することで第1の絶縁被膜を簡易に形成できる。また、原材料中に、多孔質化材、或いは上記熱硬化のための温度よりも低温で揮発する成分を含めると、第1の絶縁被膜中に微細空孔を形成し易くなる。さらに、式(1)で表される化合物の脱水縮合反応を助長する成分を含めると、Si−OH結合を減少させてシロキサン結合の密度を高め得ると共に、かかるシロキサン結合の高密度化と熱硬化によるアニール作用により第1の絶縁被膜の応力緩和を促進できる。 In this case, as a raw material of the first insulating film, it is easy to obtain a solution obtained by dissolving the compound represented by the formula (1) in a solvent (solvent). After applying the solution, hydrolysis and condensation are caused by heating. By forming and curing the siloxane resin, the first insulating film can be easily formed. In addition, if the raw material contains a porous material or a component that volatilizes at a temperature lower than the temperature for the heat curing, it is easy to form fine pores in the first insulating film. Furthermore, when a component that promotes the dehydration condensation reaction of the compound represented by the formula (1) is included, the density of siloxane bonds can be increased by reducing Si—OH bonds, and the density of siloxane bonds can be increased and thermosetting. Can promote stress relaxation of the first insulating film.
また、分子構造中にボラジン骨格を有する化合物が下記式(2);
ここで、式中、R1はアルキル基、アリール基、アラルキル基又は水素原子を示し、R2はアルキル基、アリール基、アラルキル基又は水素原子を示し、R3及びR4はアルキル基、アリール基、アラルキル基及び水素原子の中から選ばれる同一又は異なる1価の基を示し、R5は置換若しくは未置換の芳香族の2価の基、オキシポリ(ジメチルシロキシ)基、又は酸素原子を示し、R6はアルキル基、アリール基、アラルキル基又は水素原子を示し、aは正の整数を示し、bは0又は正の整数を示し、pは0又は正の整数を示し、qは0又は正の整数を示す。 Here, in the formula, R 1 represents an alkyl group, an aryl group, an aralkyl group or a hydrogen atom, R 2 represents an alkyl group, an aryl group, an aralkyl group or a hydrogen atom, and R 3 and R 4 represent an alkyl group or an aryl group. R 5 represents the same or different monovalent group selected from a group, an aralkyl group and a hydrogen atom; R 5 represents a substituted or unsubstituted aromatic divalent group, an oxypoly (dimethylsiloxy) group, or an oxygen atom; , R 6 represents an alkyl group, an aryl group, an aralkyl group or a hydrogen atom, a represents a positive integer, b represents 0 or a positive integer, p represents 0 or a positive integer, q represents 0 or Indicates a positive integer.
また、本発明による電子部品は、シリコンウェハ等の基体上に本発明による複合絶縁被膜が設けられたものである。さらに、分子構造中にボラジン骨格を含有して成る第2の絶縁被膜上に更に他の上層膜、例えばハードマスク、反射防止(AR)膜、反射膜、レジスト膜等が被着されて成る積層(構造)体も有用である。これらの上層膜のなかでも絶縁被膜上に設けられる金属配線パターンの形成に必要であり且つ強固な被着が要求されるハードマスクとの積層体が特に有用である。 電子 The electronic component according to the present invention is one in which the composite insulating coating according to the present invention is provided on a substrate such as a silicon wafer. Further, a lamination in which another upper layer film, for example, a hard mask, an anti-reflection (AR) film, a reflection film, a resist film, or the like is applied on the second insulating film containing a borazine skeleton in a molecular structure. (Structure) bodies are also useful. Among these upper layers, a laminate with a hard mask, which is necessary for forming a metal wiring pattern provided on an insulating film and requires strong adhesion, is particularly useful.
以上説明したように、本発明の複合絶縁被膜及び電子部品によれば、シロキサン樹脂を含有して成る第1の絶縁被膜上に、分子構造中にボラジン骨格を有する化合物を含有して成る第2の絶縁被膜が形成されているので、十分な低誘電率化が可能であり、しかも機械強度を高めることができ且つ上層膜との接着性を格段に高めることができ、CMP等の研磨に対する耐剥離性(CMP耐性)を向上できる。 As described above, according to the composite insulating coating and the electronic component of the present invention, the second insulating coating containing a compound having a borazine skeleton in the molecular structure is provided on the first insulating coating containing a siloxane resin. Since the insulating coating is formed, the dielectric constant can be sufficiently reduced, the mechanical strength can be increased, the adhesiveness with the upper layer can be significantly improved, and the resistance to polishing such as CMP can be improved. Peelability (CMP resistance) can be improved.
本発明の複合絶縁被膜は、シロキサン樹脂を含有して成る第1の絶縁被膜上に、分子構造中にボラジン骨格を有する化合物を含有して成る第2の絶縁被膜が形成されたものである。以下、各被膜及びその構成成分等、並びに、本発明の電子部品の好適な実施形態について説明する。 The composite insulating coating of the present invention is obtained by forming a second insulating coating containing a compound having a borazine skeleton in a molecular structure on a first insulating coating containing a siloxane resin. Hereinafter, preferred embodiments of the electronic components of the present invention and the respective coating films and the components thereof will be described.
〈第1の絶縁皮膜〉
シロキサン樹脂を含有して成る第1の絶縁被膜としては、シロキサン骨格を有するポリマーを含むものであれば特に制限されないが、好ましくは、下記式(1);
<First insulating film>
The first insulating film containing a siloxane resin is not particularly limited as long as it contains a polymer having a siloxane skeleton, but is preferably represented by the following formula (1);
X1 nSiX2 4-n …(1)、
で表される化合物を加水分解縮合して得られるシロキサン樹脂を含むシロキサン樹脂組成物の硬化物である。式(1)中、X1は、H原子若しくはF原子、又はB原子、N原子、Al原子、P原子、Si原子、Ge原子若しくはTi原子を含む基、又は炭素数1〜20の有機基を示し、X2は加水分解性基を示し、nは0〜2の整数を示し、nが2のとき、各X1は同一でも異なっていてもよく、nが0〜2のとき、各X2は同一でも異なっていてもよい。
X 1 n SiX 2 4-n (1),
Is a cured product of a siloxane resin composition containing a siloxane resin obtained by hydrolyzing and condensing a compound represented by the following formula: In the formula (1), X1 represents an H atom or an F atom, a group containing a B atom, an N atom, an Al atom, a P atom, a Si atom, a Ge atom or a Ti atom, or an organic group having 1 to 20 carbon atoms. X 2 represents a hydrolyzable group; n represents an integer of 0 to 2; when n is 2, each X 1 may be the same or different; when n is 0 to 2, each
加水分解性基X2としては、アルコキシ基、ハロゲン基、アセトキシ基、イソシアネート基、ヒドロキシル基等が挙げられる。これらの中では、第1の絶縁被膜を形成するための組成物の液状安定性や被膜塗布特性等の観点からアルコキシ基が好ましい。 The hydrolyzable group X 2, alkoxy group, halogen group, acetoxy group, an isocyanate group, a hydroxyl group, and the like. Among these, an alkoxy group is preferable from the viewpoint of the liquid stability of the composition for forming the first insulating film and the coating application characteristics.
加水分解性基X2がアルコキシ基である化合物(アルコキシシラン)としては、例えば、テトラメトキシシラン、テトラエトキシシラン、テトラ−n−プロポキシシラン、テトラ−iso−プロポキシシラン、テトラ−n−ブトキシシラン、テトラ−sec−ブトキシシラン、テトラ−tert−ブトキシシラン、テトラフェノキシシラン等のテトラアルコキシシラン、トリメトキシシラン、トリエトキシシラン、トリプロポキシシラン、フルオロトリメトキシシラン、フルオロトリエトキシシラン、メチルトリメトキシシラン、メチルトリエトキシシラン、メチルトリ−n−プロポキシシラン、メチルトリ−iso−プロポキシシラン、メチルトリ−n−ブトキシシラン、メチルトリ−iso−ブトキシシラン、メチルトリ−tert−ブトキシシラン、メチルトリフェノキシシラン、エチルトリメトキシシラン、エチルトリエトキシシラン、エチルトリ−n−プロポキシシラン、エチルトリ−iso−プロポキシシラン、エチルトリ−n−ブトキシシラン、エチルトリ−iso−ブトキシシラン、エチルトリ−tert−ブトキシシラン、エチルトリフェノキシシラン、n−プロピルトリメトキシシラン、n−プロピルトリエトキシシラン、n−プロピルトリ−n−プロポキシシラン、n−プロピルトリ−iso−プロポキシシラン、n−プロピルトリ−n−ブトキシシラン、n−プロピルトリ−iso−ブトキシシラン、n−プロピルトリ−tert−ブトキシシラン、n−プロピルトリフェノキシシラン、iso−プロピルトリメトキシシラン、iso−プロピルトリエトキシシラン、iso−プロピルトリ−n−プロポキシシラン、iso−プロピルトリ−iso−プロポキシシラン、iso−プロピルトリ−n−ブトキシシラン、iso−プロピルトリ−iso−ブトキシシラン、iso−プロピルトリ−tert−ブトキシシラン、iso−プロピルトリフェノキシシラン、n−ブチルトリメトキシシラン、n−ブチルトリエトキシシラン、n−ブチルトリ−n−プロポキシシラン、n−ブチルトリ−iso−プロポキシシラン、n−ブチルトリ−n−ブトキシシラン、n−ブチルトリ−iso−ブトキシシラン、n−ブチルトリ−tert−ブトキシシラン、n−ブチルトリフェノキシシラン、sec−ブチルトリメトキシシラン、sec−ブチルトリエトキシシラン、sec−ブチルトリ−n−プロポキシシラン、sec−ブチルトリ−iso−プロポキシシラン、sec−ブチルトリ−n−ブトキシシラン、sec−ブチルトリ−iso−ブトキシシラン、sec−ブチルトリ−tert−ブトキシシラン、sec−ブチルトリフェノキシシラン、t−ブチルトリメトキシシラン、t−ブチルトリエトキシシラン、t−ブチルトリ−n−プロポキシシラン、t−ブチルトリ−iso−プロポキシシラン、t−ブチルトリ−n−ブトキシシラン、t−ブチルトリ−iso−ブトキシシラン、t−ブチルトリ−tert−ブトキシシラン、t−ブチルトリフェノキシシラン、フェニルトリメトキシシラン、フェニルトリエトキシシラン、フェニルトリ−n−プロポキシシラン、フェニルトリ−iso−プロポキシシラン、フェニルトリ−n−ブトキシシラン、フェニルトリ−iso−ブトキシシラン、フェニルトリ−tert−ブトキシシラン、フェニルトリフェノキシシラン、トリフルオロメチルトリメトキシシラン、ペンタフルオロエチルトリメトキシシラン、3,3,3−トリフルオロプロピルトリメトキシシラン、3,3,3−トリフルオロプロピルトリエトキシシラン等のトリアルコキシシラン、ジメチルジメトキシシラン、ジメチルジエトキシシラン、ジメチルジ−n−プロポキシシラン、ジメチルジ−iso−プロポキシシラン、ジメチルジ−n−ブトキシシラン、ジメチルジ−sec−ブトキシシラン、ジメチルジ−tert−ブトキシシラン、ジメチルジフェノキシシラン、ジエチルジメトキシシラン、ジエチルジエトキシシラン、ジエチルジ−n−プロポキシシラン、ジエチルジ−iso−プロポキシシラン、ジエチルジ−n−ブトキシシラン、ジエチルジ−sec−ブトキシシラン、ジエチルジ−tert−ブトキシシラン、ジエチルジフェノキシシラン、ジ−n−プロピルジメトキシシラン、ジ−n−プロピルジエトキシシラン、ジ−n−プロピルジ−n−プロポキシシラン、ジ−n−プロピルジ−iso−プロポキシシラン、ジ−n−プロピルジ−n−ブトキシシラン、ジ−n−プロピルジ−sec−ブトキシシラン、ジ−n−プロピルジ−tert−ブトキシシラン、ジ−n−プロピルジフェノキシシラン、ジ−iso−プロピルジメトキシシラン、ジ−iso−プロピルジエトキシシラン、ジ−iso−プロピルジ−n−プロポキシシラン、ジ−iso−プロピルジ−iso−プロポキシシラン、ジ−iso−プロピルジ−n−ブトキシシラン、ジ−iso−プロピルジ−sec−ブトキシシラン、ジ−iso−プロピルジ−tert−ブトキシシラン、ジ−iso−プロピルジフェノキシシラン、ジ−n−ブチルジメトキシシラン、ジ−n−ブチルジエトキシシラン、ジ−n−ブチルジ−n−プロポキシシラン、ジ−n−ブチルジ−iso−プロポキシシラン、ジ−n−ブチルジ−n−ブトキシシラン、ジ−n−ブチルジ−sec−ブトキシシラン、ジ−n−ブチルジ−tert−ブトキシシラン、ジ−n−ブチルジフェノキシシラン、ジ−sec−ブチルジメトキシシラン、ジ−sec−ブチルジエトキシシラン、ジ−sec−ブチルジ−n−プロポキシシラン、ジ−sec−ブチルジ−iso−プロポキシシラン、ジ−sec−ブチルジ−n−ブトキシシラン、ジ−sec−ブチルジ−sec−ブトキシシラン、ジ−sec−ブチルジ−tert−ブトキシシラン、ジ−sec−ブチルジフェノキシシラン、ジ−tert−ブチルジメトキシシラン、ジ−tert−ブチルジエトキシシラン、ジ−tert−ブチルジ−n−プロポキシシラン、ジ−tert−ブチルジ−iso−プロポキシシラン、ジ−tert−ブチルジ−n−ブトキシシラン、ジ−tert−ブチルジ−sec−ブトキシシラン、ジ−tert−ブチルジ−tert−ブトキシシラン、ジ−tert−ブチルジフェノキシシラン、ジフェニルジメトキシシラン、ジフェニルジエトキシシラン、ジフェニルジ−n−プロポキシシラン、ジフェニルジ−iso−プロポキシシラン、ジフェニルジ−n−ブトキシシラン、ジフェニルジ−sec−ブトキシシラン、ジフェニルジ−tert−ブトキシシラン、ジフェニルジフェノキシシラン、ビス(3,3,3−トリフルオロプロピル)ジメトキシシラン、メチル(3,3,3−トリフルオロプロピル)ジメトキシシラン等のジオルガノジアルコキシシラン等が挙げられる。 Examples of the compound in which the hydrolyzable group X 2 is an alkoxy group (alkoxysilane) include, for example, tetramethoxysilane, tetraethoxysilane, tetra-n-propoxysilane, tetra-iso-propoxysilane, tetra-n-butoxysilane, Tetra-sec-butoxysilane, tetra-tert-butoxysilane, tetraalkoxysilane such as tetraphenoxysilane, trimethoxysilane, triethoxysilane, tripropoxysilane, fluorotrimethoxysilane, fluorotriethoxysilane, methyltrimethoxysilane, Methyltriethoxysilane, methyltri-n-propoxysilane, methyltri-iso-propoxysilane, methyltri-n-butoxysilane, methyltri-iso-butoxysilane, methyltri-tert-butyl Xysilane, methyltriphenoxysilane, ethyltrimethoxysilane, ethyltriethoxysilane, ethyltri-n-propoxysilane, ethyltri-iso-propoxysilane, ethyltri-n-butoxysilane, ethyltri-iso-butoxysilane, ethyltri-tert-butoxy Silane, ethyltriphenoxysilane, n-propyltrimethoxysilane, n-propyltriethoxysilane, n-propyltri-n-propoxysilane, n-propyltri-iso-propoxysilane, n-propyltri-n-butoxysilane , N-propyltri-iso-butoxysilane, n-propyltri-tert-butoxysilane, n-propyltriphenoxysilane, iso-propyltrimethoxysilane, iso-propyltriethoxy Sisilane, iso-propyltri-n-propoxysilane, iso-propyltri-iso-propoxysilane, iso-propyltri-n-butoxysilane, iso-propyltri-iso-butoxysilane, iso-propyltri-tert-butoxy Silane, iso-propyltriphenoxysilane, n-butyltrimethoxysilane, n-butyltriethoxysilane, n-butyltri-n-propoxysilane, n-butyltri-iso-propoxysilane, n-butyltri-n-butoxysilane, n-butyltri-iso-butoxysilane, n-butyltri-tert-butoxysilane, n-butyltriphenoxysilane, sec-butyltrimethoxysilane, sec-butyltriethoxysilane, sec-butyltri-n-propoxy Silane, sec-butyltri-iso-propoxysilane, sec-butyltri-n-butoxysilane, sec-butyltri-iso-butoxysilane, sec-butyltri-tert-butoxysilane, sec-butyltriphenoxysilane, t-butyltrimethoxy Silane, t-butyltriethoxysilane, t-butyltri-n-propoxysilane, t-butyltri-iso-propoxysilane, t-butyltri-n-butoxysilane, t-butyltri-iso-butoxysilane, t-butyltri-tert -Butoxysilane, t-butyltriphenoxysilane, phenyltrimethoxysilane, phenyltriethoxysilane, phenyltri-n-propoxysilane, phenyltri-iso-propoxysilane, phenyltri-n-but Silane, phenyltri-iso-butoxysilane, phenyltri-tert-butoxysilane, phenyltriphenoxysilane, trifluoromethyltrimethoxysilane, pentafluoroethyltrimethoxysilane, 3,3,3-trifluoropropyltrimethoxysilane, Trialkoxysilanes such as 3,3,3-trifluoropropyltriethoxysilane, dimethyldimethoxysilane, dimethyldiethoxysilane, dimethyldi-n-propoxysilane, dimethyldi-iso-propoxysilane, dimethyldi-n-butoxysilane, dimethyldi- sec-butoxysilane, dimethyldi-tert-butoxysilane, dimethyldiphenoxysilane, diethyldimethoxysilane, diethyldiethoxysilane, diethyldi-n-propoxysilane , Diethyldi-iso-propoxysilane, diethyldi-n-butoxysilane, diethyldi-sec-butoxysilane, diethyldi-tert-butoxysilane, diethyldiphenoxysilane, di-n-propyldimethoxysilane, di-n-propyldiethoxysilane Di-n-propyldi-n-propoxysilane, di-n-propyldi-iso-propoxysilane, di-n-propyldi-n-butoxysilane, di-n-propyldi-sec-butoxysilane, di-n-propyldi -Tert-butoxysilane, di-n-propyldiphenoxysilane, di-iso-propyldimethoxysilane, di-iso-propyldiethoxysilane, di-iso-propyldi-n-propoxysilane, di-iso-propyldi-iso -Propoxysilane Di-iso-propyldi-n-butoxysilane, di-iso-propyldi-sec-butoxysilane, di-iso-propyldi-tert-butoxysilane, di-iso-propyldiphenoxysilane, di-n-butyldimethoxysilane, Di-n-butyldiethoxysilane, di-n-butyldi-n-propoxysilane, di-n-butyldi-iso-propoxysilane, di-n-butyldi-n-butoxysilane, di-n-butyldi-sec- Butoxysilane, di-n-butyldi-tert-butoxysilane, di-n-butyldiphenoxysilane, di-sec-butyldimethoxysilane, di-sec-butyldiethoxysilane, di-sec-butyldi-n-propoxysilane , Di-sec-butyldi-iso-propoxysilane, di-sec- Tildi-n-butoxysilane, di-sec-butyldi-sec-butoxysilane, di-sec-butyldi-tert-butoxysilane, di-sec-butyldiphenoxysilane, di-tert-butyldimethoxysilane, di-tert- Butyldiethoxysilane, di-tert-butyldi-n-propoxysilane, di-tert-butyldi-iso-propoxysilane, di-tert-butyldi-n-butoxysilane, di-tert-butyldi-sec-butoxysilane, di- -Tert-butyldi-tert-butoxysilane, di-tert-butyldiphenoxysilane, diphenyldimethoxysilane, diphenyldiethoxysilane, diphenyldi-n-propoxysilane, diphenyldi-iso-propoxysilane, diphenyldi-n-butyl Toxysilane, diphenyldi-sec-butoxysilane, diphenyldi-tert-butoxysilane, diphenyldiphenoxysilane, bis (3,3,3-trifluoropropyl) dimethoxysilane, methyl (3,3,3-trifluoropropyl) And diorganodialkoxysilanes such as dimethoxysilane.
また、上記のアルコキシシランの他に、上記式(1)で表される化合物として、上記のアルコキシシラン分子中のアルコキシ基がハロゲン原子で置換されたハロゲンシラン類、同アルコキシ基がアセトキシ基で置換されたアセトキシシラン類、同アルコキシ基がイソシアネート基で置換されたイソシアネートシラン類、同アルコキシ基がヒドロキシル基で置換されたシラノール類等が挙げられる。式(1)で表されるこれらの化合物は単独で用いてもよく、或いは2種以上組み合わせて用いてもよい。 In addition to the above-mentioned alkoxysilanes, compounds represented by the above formula (1) include halogensilanes in which the alkoxy groups in the alkoxysilane molecules are substituted with halogen atoms, and the alkoxy groups in the alkoxysilane molecules are substituted with acetoxy groups. Acetoxysilanes, isocyanate silanes in which the alkoxy group is substituted with an isocyanate group, silanols in which the alkoxy group is substituted with a hydroxyl group, and the like. These compounds represented by the formula (1) may be used alone or in combination of two or more.
また、式(1)で表される化合物の加水分解縮合においては、加水分解縮合反応を促進する触媒として、酸触媒又は塩基触媒を使用できる。酸触媒としては、蟻酸、マレイン酸、フマル酸、酢酸、プロピオン酸、ブタン酸、ペンタン酸、ヘキサン酸、ヘプタン酸、オクタン酸、ノナン酸、デカン酸、シュウ酸、アジピン酸、セバシン酸、酪酸、オレイン酸、ステアリン酸、リノール酸、リノレイン酸、サリチル酸、安息香酸、p−アミノ安息香酸、p−トルエンスルホン酸、フタル酸、スルホン酸、酒石酸、トリフルオロメタンスルフォン酸等の有機酸、塩酸、燐酸、硝酸、ホウ酸、硫酸、フッ酸等が挙げられる。また、塩基触媒としては、アンモニア、有機アミン類等を例示できる。 In addition, in the hydrolysis and condensation of the compound represented by the formula (1), an acid catalyst or a base catalyst can be used as a catalyst for promoting the hydrolysis and condensation reaction. Acid catalysts include formic acid, maleic acid, fumaric acid, acetic acid, propionic acid, butanoic acid, pentanoic acid, hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, oxalic acid, adipic acid, sebacic acid, butyric acid, Oleic acid, stearic acid, linoleic acid, linoleic acid, salicylic acid, benzoic acid, p-aminobenzoic acid, p-toluenesulfonic acid, phthalic acid, sulfonic acid, tartaric acid, organic acids such as trifluoromethanesulfonic acid, hydrochloric acid, phosphoric acid, Examples include nitric acid, boric acid, sulfuric acid, and hydrofluoric acid. Examples of the basic catalyst include ammonia and organic amines.
このような加水分解縮合反応を促進する触媒は、式(1)で表される化合物1モルに対して0.0001〜1モルの範囲で使用されると好ましい。この使用量が0.0001未満であると、重合反応が十分に進行しない傾向にある。一方、この使用量が1モルを超えると、ゲル化が促進される傾向にあり好ましくない。 触媒 The catalyst for promoting the hydrolysis-condensation reaction is preferably used in the range of 0.0001 to 1 mol per 1 mol of the compound represented by the formula (1). If the amount is less than 0.0001, the polymerization reaction tends to not sufficiently proceed. On the other hand, if the amount exceeds 1 mol, gelation tends to be promoted, which is not preferable.
また、加水分解縮合反応で副生するアルコールは、必要に応じてエバポレータ等により除去してもよい。さらに、加水分解縮合反応系中の水の量は適宜決定することができ、式(1)で表される化合物1モルに対して0.5〜20モルの範囲とすることが好ましい。この水の量が0.5〜20モルの範囲を外れると、成膜性が悪化したり、保存安定性が低下するといった不都合がある。 ア ル コ ー ル Also, alcohol by-produced in the hydrolysis condensation reaction may be removed by an evaporator or the like as necessary. Further, the amount of water in the hydrolysis-condensation reaction system can be appropriately determined, and is preferably in the range of 0.5 to 20 mol per 1 mol of the compound represented by the formula (1). If the amount of water is out of the range of 0.5 to 20 mol, there are inconveniences such as poor film formability and low storage stability.
さらに、式(1)で表される化合物を加水分解縮合して得られるシロキサン樹脂は、溶媒への溶解性、機械特性、成形性等の観点から、ゲルパーミエーションクロマトグラフィー(GPC)により測定し、標準ポリスチレンの検量線を使用して換算した値の重量平均分子量が、500〜20,000であることが好ましく、1,000〜10,000であるとより好ましい。 Furthermore, the siloxane resin obtained by hydrolyzing and condensing the compound represented by the formula (1) is measured by gel permeation chromatography (GPC) from the viewpoint of solubility in a solvent, mechanical properties, moldability, and the like. The weight average molecular weight of the value converted using a calibration curve of standard polystyrene is preferably from 500 to 20,000, more preferably from 1,000 to 10,000.
またさらに、第1の絶縁被膜を構成するシロキサン樹脂組成物は、通常、溶媒を必須成分として含有する。かかる溶媒としては、例えば、メタノール、エタノール、n−プロパノール、i−プロパノール、n−ブタノール、i−ブタノール、sec−ブタノール、t−ブタノール、n−ペンタノール、i−ペンタノール、2−メチルブタノール、sec−ペンタノール、t−ペンタノール、3−メトキシブタノール、n−ヘキサノール、2−メチルペンタノール、sec−ヘキサノール、2−エチルブタノール、sec−ヘプタノール、n−オクタノール、2−エチルヘキサノール、sec−オクタノール、n−ノニルアルコール、n−デカノール、sec−ウンデシルアルコール、トリメチルノニルアルコール、sec−テトラデシルアルコール、sec−ヘプタデシルアルコール、フェノール、シクロヘキサノール、メチルシクロヘキサノール、ベンジルアルコール、エチレングリコール、1,2−プロピレングリコール、1,3−ブチレングリコール、ジエチレングリコール、ジプロピレングリコール、トリエチレングリコール、トリプロピレングリコール等のアルコール系、アセトン、メチルエチルケトン、メチル−n−プロピルケトン、メチル−n−ブチルケトン、メチル−iso−ブチルケトン、メチル−n−ペンチルケトン、メチル−n−ヘキシルケトン、ジエチルケトン、ジ−iso−ブチルケトン、トリメチルノナノン、シクロヘキサノン、シクロペンタノン、メチルシクロヘキサノン、2,4−ペンタンジオン、アセトニルアセトン、ジアセトンアルコール、アセトフェノン、γ−ブチロラクトン等のケトン系溶媒、エチルエーテル、iso−プロピルエーテル、n−ブチルエーテル、n−ヘキシルエーテル、2−エチルヘキシルエーテル、エチレンオキシド、1,2−プロピレンオキシド、ジオキソラン、4−メチルジオキソラン、ジオキサン、ジメチルジオキサン、エチレングリコールモノメチルエーテル、エチレングリコールモノエチルエーテル、エチレングリコールジエチルエーテル、エチレングリコールモノ−n−ヘキシルエーテル、エチレングリコールモノフェニルエーテル、エチレングリコールモノ−2−エチルブチルエーテル、エチレングリコールジブチルエーテル、ジエチレングリコールモノエチルエーテル、ジエチレングリコールジエチルエーテル、ジエチレングリコールジエチルエーテル、ジエチレングリコールモノ−n−ブチルエーテル、ジエチレングリコールジ−n−ブチルエーテル、ジエチレングリコールモノ−n−ヘキシルエーテル、エトキシトリグリコール、テトラエチレングリコールジ−n−ブチルエーテル、プロピレングリコールモノメチルエーテル、プロピレングリコールモノエチルエーテル、プロピレングリコールモノプロピルエーテル、ジプロピレングリコールモノメチルエーテル、ジプロピレングリコールモノエチルエーテル、トリプロピレングリコールモノメチルエーテル、テトラヒドロフラン、2−メチルテトラヒドロフラン等のエーテル系溶媒、酢酸メチル、酢酸エチル、酢酸n−プロピル、酢酸i−プロピル、酢酸n−ブチル、酢酸i−ブチル、酢酸sec−ブチル、酢酸n−ペンチル、酢酸sec−ペンチル、酢酸3−メトキシブチル、酢酸メチルペンチル、酢酸2−エチルブチル、酢酸2−エチルヘキシル、酢酸ベンジル、酢酸シクロヘキシル、酢酸メチルシクロヘキシル、酢酸ノニル、γ−ブチロラクトン、γ−バレロラクトン、アセト酢酸メチル、アセト酢酸エチル、酢酸エチレングリコールモノメチルエーテル、酢酸エチレングリコールモノエチルエーテル、酢酸ジエチレングリコールモノメチルエーテル、酢酸ジエチレングリコールモノエチルエーテル、酢酸ジエチレングリコールモノ−n−ブチルエーテル、酢酸プロピレングリコールモノメチルエーテル、酢酸プロピレングリコールモノエチルエーテル、酢酸プロピレングリコールモノプロピルエーテル、酢酸ジプロピレングリコールモノメチルエーテル、酢酸ジプロピレングリコールモノエチルエーテル、ジ酢酸グリコール、酢酸メトキシトリグリコール、プロピオン酸エチル、プロピオン酸n−ブチル、プロピオン酸i−アミル、シュウ酸ジエチル、シュウ酸ジ−n−ブチル、乳酸メチル、乳酸エチル、乳酸n−ブチル、乳酸n−アミル等のエステル系溶媒、アセトニトリル、N,N−ジメチルホルムアミド、N,N−ジメチルアセトアミド、N,N−ジメチルスルホキシド等が挙げられ、これらは単独で又は2種以上を組み合わせて用いられる。 Furthermore, the siloxane resin composition constituting the first insulating film usually contains a solvent as an essential component. Examples of such a solvent include methanol, ethanol, n-propanol, i-propanol, n-butanol, i-butanol, sec-butanol, t-butanol, n-pentanol, i-pentanol, 2-methylbutanol, sec-pentanol, t-pentanol, 3-methoxybutanol, n-hexanol, 2-methylpentanol, sec-hexanol, 2-ethylbutanol, sec-heptanol, n-octanol, 2-ethylhexanol, sec-octanol , N-nonyl alcohol, n-decanol, sec-undecyl alcohol, trimethylnonyl alcohol, sec-tetradecyl alcohol, sec-heptadecyl alcohol, phenol, cyclohexanol, methylcyclohexanol Alcohols such as benzyl alcohol, ethylene glycol, 1,2-propylene glycol, 1,3-butylene glycol, diethylene glycol, dipropylene glycol, triethylene glycol, tripropylene glycol, acetone, methyl ethyl ketone, methyl-n-propyl ketone, methyl -N-butyl ketone, methyl-iso-butyl ketone, methyl-n-pentyl ketone, methyl-n-hexyl ketone, diethyl ketone, di-iso-butyl ketone, trimethylnonanone, cyclohexanone, cyclopentanone, methylcyclohexanone, 2,4 -Ketone solvents such as pentanedione, acetonylacetone, diacetone alcohol, acetophenone, γ-butyrolactone, ethyl ether, iso-propyl ether, n- Butyl ether, n-hexyl ether, 2-ethylhexyl ether, ethylene oxide, 1,2-propylene oxide, dioxolane, 4-methyldioxolane, dioxane, dimethyldioxane, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol diethyl ether, ethylene Glycol mono-n-hexyl ether, ethylene glycol monophenyl ether, ethylene glycol mono-2-ethylbutyl ether, ethylene glycol dibutyl ether, diethylene glycol monoethyl ether, diethylene glycol diethyl ether, diethylene glycol diethyl ether, diethylene glycol mono-n-butyl ether, diethylene glycol di -N-butyl a , Diethylene glycol mono-n-hexyl ether, ethoxytriglycol, tetraethylene glycol di-n-butyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, dipropylene glycol monomethyl ether, dipropylene glycol mono Ether solvents such as ethyl ether, tripropylene glycol monomethyl ether, tetrahydrofuran and 2-methyltetrahydrofuran; methyl acetate, ethyl acetate, n-propyl acetate, i-propyl acetate, n-butyl acetate, i-butyl acetate, sec-acetic acid Butyl, n-pentyl acetate, sec-pentyl acetate, 3-methoxybutyl acetate, methylpentyl acetate, 2-ethylbutyl acetate, acetic acid -Ethylhexyl, benzyl acetate, cyclohexyl acetate, methylcyclohexyl acetate, nonyl acetate, γ-butyrolactone, γ-valerolactone, methyl acetoacetate, ethyl acetoacetate, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monomethyl acetate acetate , Diethylene glycol monoethyl ether acetate, diethylene glycol mono-n-butyl ether acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, dipropylene glycol monomethyl ether acetate, dipropylene glycol monoethyl acetate acetate, Glycol diacetate, methoxytriglycol acetate, Ester solvents such as ethyl acetate, n-butyl propionate, i-amyl propionate, diethyl oxalate, di-n-butyl oxalate, methyl lactate, ethyl lactate, n-butyl lactate, n-amyl lactate, and acetonitrile , N, N-dimethylformamide, N, N-dimethylacetamide, N, N-dimethylsulfoxide and the like, which are used alone or in combination of two or more.
シロキサン樹脂組成物における溶媒の使用量は、シロキサン樹脂の濃度が3〜25質量%となるような量とすることが好ましい。この溶媒使用量が過度に少なくシロキサン樹脂濃度が25質量%を超えると、液状安定性、成膜性等が不都合な程に劣る傾向にある。一方、この溶媒使用量が過度に多くシロキサン樹脂濃度が3質量%未満となると、所望の膜厚の第1の絶縁被膜を得ることが困難な傾向にある。 (4) The amount of the solvent used in the siloxane resin composition is preferably such that the concentration of the siloxane resin is 3 to 25% by mass. If the amount of the solvent is excessively small and the siloxane resin concentration exceeds 25% by mass, the liquid stability, film formability, and the like tend to be inadequately deteriorated. On the other hand, when the amount of the solvent used is excessively large and the siloxane resin concentration is less than 3% by mass, it tends to be difficult to obtain a first insulating film having a desired film thickness.
本発明のシロキサン樹脂組成物には、必要に応じて多孔質化材を添加することができる。多孔質化材の具体例としては、アクリル酸、2−ヒドロキシエチルアクリレート、ジエチレングリコールアクリレート、2−ヒドロキシプロピルアクリレート、ジプロピレングリコールアクリレート、メタクリル酸、2−ヒドロキシエチルメタクリレート、ジエチレングリコールメタクリレート、2−ヒドロキシプロピルメタクリレート、ジプロピレングリコールメタクリレート等の(メタ)アクリル酸誘導体、ビニルアルコール、アリルアルコールビニルエーテル系化合物、ポリエチレンオキサイド構造を有するビニル系化合物、ポリプロピレンオキサイド構造を有するビニル系化合物、ビニルピリジン系化合物、スチレン系化合物、アルキルエステルビニル系化合物、(メタ)アクリレート酸系化合物、プロピレングリコール系化合物、エチレングリコール系化合物等の重合体が挙げられる。 多孔 A porous material can be added to the siloxane resin composition of the present invention as needed. Specific examples of the porous material include acrylic acid, 2-hydroxyethyl acrylate, diethylene glycol acrylate, 2-hydroxypropyl acrylate, dipropylene glycol acrylate, methacrylic acid, 2-hydroxyethyl methacrylate, diethylene glycol methacrylate, and 2-hydroxypropyl methacrylate. (Meth) acrylic acid derivatives such as dipropylene glycol methacrylate, vinyl alcohol, allyl alcohol vinyl ether compound, vinyl compound having a polyethylene oxide structure, vinyl compound having a polypropylene oxide structure, vinyl pyridine compound, styrene compound, Alkyl ester vinyl compound, (meth) acrylate acid compound, propylene glycol compound, Polymers such as Chi glycol-based compounds.
〈第2の絶縁被膜〉
第2の絶縁被膜は、分子構造中にボラジン骨格を有する化合物を含んでおり、この化合物としては主鎖又は側鎖に置換又は無置換のボラジン骨格を有するものであればよく、ボラジン化合物の単量体及び重合体のいずれでもよく、第2の絶縁被膜の成膜性や膜強度の観点から重合体を使用することが望ましい。このような重合体としては、例えば、Chemical Review 誌、vol 90、pp.73〜91(1990).やCHEMTECH 誌、1994年7月、pp.29〜37.記載の重合体等を挙げることができる。具体的には以下に示す重合体が好適である。
The second insulating coating contains a compound having a borazine skeleton in its molecular structure, and any compound having a substituted or unsubstituted borazine skeleton in the main chain or side chain may be used. Either a polymer or a polymer may be used, and it is desirable to use a polymer from the viewpoint of film formability and film strength of the second insulating film. Examples of such a polymer include, for example, Chemical Review, vol. 73-91 (1990). And CHEMTECH, July 1994, pp. 29-37. And the like. Specifically, the following polymers are suitable.
また、好ましくは、下記式(2)又は式(3);
なお、式(2)及び(3)において、
そして、
また、式(2)における破線は、ボラジン残基におけるアルキニル基由来の炭素に結合が生じていることを意味し、式(3)における破線は、ボラジン残基におけるアルケニル基由来の炭素に結合が生じていることを意味する。 Further, the broken line in the formula (2) means that a bond is formed at the carbon derived from the alkynyl group in the borazine residue, and the broken line in the formula (3) is a bond formed at the carbon derived from the alkenyl group in the borazine residue. Means that it has occurred.
また、式(2)及び(3)において、R1はアルキル基、アリール基、アラルキル基又は水素原子を示す。この場合、アルキル基の炭素数は1〜24、好ましくは1〜12である。また、アリール基の炭素数は6〜20、好ましくは6〜10である。さらに、アラルキル基の炭素数は7〜24、好ましくは7〜12である。より具体的には、基R1として、メチル基、エチル基、イソプロピル基、t−ブチル基、オクチル基等のアルキル基、フェニル基、ナフチル基、ビフェニル基等のアリール基、ベンジル基、フェネチル基等のアラルキル基、水素原子等が挙げられ、これらの中では、メチル基、エチル基、フェニル基又は水素原子がより好ましい。 In the formulas (2) and (3), R 1 represents an alkyl group, an aryl group, an aralkyl group or a hydrogen atom. In this case, the alkyl group has 1 to 24, preferably 1 to 12 carbon atoms. The aryl group has 6 to 20 carbon atoms, preferably 6 to 10 carbon atoms. Further, the aralkyl group has 7 to 24 carbon atoms, preferably 7 to 12 carbon atoms. More specifically, as the group R 1 , an alkyl group such as a methyl group, an ethyl group, an isopropyl group, a t-butyl group, an octyl group, an aryl group such as a phenyl group, a naphthyl group, a biphenyl group, a benzyl group, and a phenethyl group And the like. Among them, a methyl group, an ethyl group, a phenyl group or a hydrogen atom is more preferable.
また、式(2)及び(3)において、R2はアルキル基、アリール基、アラルキル基又は水素原子を示し、アルキル基の炭素数は1〜24、好ましくは1〜12である。この場合、アリール基の炭素数は6〜20、好ましくは6〜10である。また、アラルキル基の炭素数は7〜24、好ましくは7〜12である。より具体的には、基R2として、メチル基、エチル基、イソプロピル基、t−ブチル基、オクチル基等のアルキル基、フェニル基、ナフチル基、ビフェニル基、アントラセニル基等のアリール基、ベンジル基、フェネチル基、フルオレニル基等のアラルキル基、水素原子等が挙げられ、これらの中では、メチル基、フェニル基又は水素原子がより好ましい。 In the formulas (2) and (3), R 2 represents an alkyl group, an aryl group, an aralkyl group or a hydrogen atom, and the alkyl group has 1 to 24, preferably 1 to 12 carbon atoms. In this case, the aryl group has 6 to 20, preferably 6 to 10 carbon atoms. The aralkyl group has 7 to 24 carbon atoms, preferably 7 to 12 carbon atoms. More specifically, as the group R 2 , an alkyl group such as a methyl group, an ethyl group, an isopropyl group, a t-butyl group, an octyl group, an aryl group such as a phenyl group, a naphthyl group, a biphenyl group and an anthracenyl group, and a benzyl group And an aralkyl group such as a phenethyl group and a fluorenyl group, and a hydrogen atom. Of these, a methyl group, a phenyl group and a hydrogen atom are more preferable.
さらに、式(2)及び(3)において、R3及びR4はアルキル基、アリール基、アラルキル基又は水素原子の中から選ばれる同一又は異なる1価の基を示し、これらの中では、アルキル基、アリール基又は水素原子がより好ましい。この場合、アルキル基の炭素数は1〜24、好ましくは1〜12である。また、アリール基の炭素数は6〜20、好ましくは6〜10である。さらに、アラルキル基の炭素数は7〜24、好ましくは7〜12である。より具体的には、基R3及びR4として、メチル基、エチル基、イソプロピル基、t−ブチル基、オクチル基等のアルキル基、フェニル基、ナフチル基、ビフェニル基等のアリール基、ベンジル基、フェネチル基等のアラルキル基、水素原子等が挙げられ、これらの中ではメチル基、フェニル基又は水素原子がより好ましい。 Further, in the formulas (2) and (3), R 3 and R 4 represent the same or different monovalent groups selected from an alkyl group, an aryl group, an aralkyl group and a hydrogen atom. Groups, aryl groups or hydrogen atoms are more preferred. In this case, the alkyl group has 1 to 24, preferably 1 to 12 carbon atoms. The aryl group has 6 to 20 carbon atoms, preferably 6 to 10 carbon atoms. Further, the aralkyl group has 7 to 24 carbon atoms, preferably 7 to 12 carbon atoms. More specifically, as groups R 3 and R 4 , alkyl groups such as methyl group, ethyl group, isopropyl group, t-butyl group, octyl group, aryl groups such as phenyl group, naphthyl group, biphenyl group, and benzyl group And an aralkyl group such as a phenethyl group, a hydrogen atom and the like. Among them, a methyl group, a phenyl group and a hydrogen atom are more preferable.
またさらに、式(2)及び(3)において、R5は置換若しくは未置換の芳香族の2価の基、オキシポリ(ジメチルシロキシ)基、又は酸素原子を示す。この場合、芳香族の2価の基の炭素数は6〜24、好ましくは6〜12である。この芳香族の2価の基には、2価芳香族炭化水素基(アリーレン基等)の他、酸素等のヘテロ原子を連結基として含むアリーレン基等が含まれる。また、この芳香族の2価の基に結合していてもよい置換基としては、アルキル基、アリール基、アラルキル基等が挙げられる。より具体的には、基R5として、フェニレン基、ナフチレン基、ビフェニレン基等のアリーレン基、ジフェニルエーテル基等の置換アリーレン基、酸素原子等が挙げられ、これらの中ではフェニレン基、ジフェニルエーテル基又は酸素原子がより好ましい。 Further, in the formulas (2) and (3), R 5 represents a substituted or unsubstituted aromatic divalent group, an oxypoly (dimethylsiloxy) group, or an oxygen atom. In this case, the aromatic divalent group has 6 to 24 carbon atoms, preferably 6 to 12 carbon atoms. The aromatic divalent group includes, in addition to a divalent aromatic hydrocarbon group (such as an arylene group), an arylene group containing a heteroatom such as oxygen as a linking group. Examples of the substituent that may be bonded to the aromatic divalent group include an alkyl group, an aryl group, and an aralkyl group. More specifically, as the base R 5, a phenylene group, a naphthylene group, an arylene group such as biphenylene group, a substituted arylene group such as diphenyl ether group, such as an oxygen atom., A phenylene group, diphenyl ether group or oxygen among these Atoms are more preferred.
さらにまた、式(2)及び(3)において、R6はアルキル基、アリール基又はアラルキル基を示す。この場合、アルキル基の炭素数は1〜24、好ましくは1〜12である。また、アリール基の炭素数は6〜20、好ましくは6〜10である。さらに、アラルキル基の炭素数は7〜24、好ましくは7〜12である。より具体的には、基R6として、メチル基、エチル基、イソプロピル基、t−ブチル基、オクチル基等のアルキル基、フェニル基、ナフチル基、ビフェニル基等のアリール基、ベンジル基、フェネチル基等のアラルキル基等が挙げられる。 Further, in the formulas (2) and (3), R 6 represents an alkyl group, an aryl group or an aralkyl group. In this case, the alkyl group has 1 to 24, preferably 1 to 12 carbon atoms. The aryl group has 6 to 20 carbon atoms, preferably 6 to 10 carbon atoms. Further, the aralkyl group has 7 to 24 carbon atoms, preferably 7 to 12 carbon atoms. More specifically, as the group R 6 , an alkyl group such as a methyl group, an ethyl group, an isopropyl group, a t-butyl group, an octyl group, an aryl group such as a phenyl group, a naphthyl group, a biphenyl group, a benzyl group, a phenethyl group And the like.
また、式(2)及び(3)において、a及びbは、それぞれ繰り返し単位数を表し、aは正の整数であって、好ましくは1〜20000、より好ましくは3〜10000であり、特に好ましくは5〜10000である。また、bは0又は正の整数であって、好ましくは0〜1000、より好ましくは0〜100である。ただし、a及びbはそれらの構成比率を示すものであって、結合状態(ブロック共重合、ランダム共重合等)のいずれかの形態に限定されるものではない。 In the formulas (2) and (3), a and b each represent the number of repeating units, and a is a positive integer, preferably 1 to 20,000, more preferably 3 to 10,000, and particularly preferably. Is 5 to 10,000. B is 0 or a positive integer, preferably 0 to 1000, more preferably 0 to 100. However, a and b indicate their constituent ratios, and are not limited to any form of the bonding state (block copolymerization, random copolymerization, etc.).
このような共重合体において、aとbとのそれぞれの個数の比(a:b)は特に制限されず、a/b比がより大きい、つまり高分子主鎖中の鎖状構造の割合が比較的多い場合、溶媒に対する共重合体の溶解度が高められ且つ融点が低くなることにより、共重合体の加工性が向上すると予想される。一方、a/b比がより小さい、つまり高分子主鎖中の架橋構造の割合が比較的多い場合、共重合体の耐熱性、耐燃焼性が向上すると予想される。したがって、用途等に応じて、或いは、共重合体の各モノマーユニットの構造及びその組み合わせに応じて、良好な加工性及び耐熱性、耐燃焼性を与える共重合体の最適なa/b比の範囲を適宜設定することができる。 In such a copolymer, the ratio (a: b) of the respective numbers of a and b is not particularly limited, and the a / b ratio is large, that is, the ratio of the chain structure in the polymer main chain is low. When the amount is relatively large, it is expected that the processability of the copolymer will be improved by increasing the solubility of the copolymer in the solvent and lowering the melting point. On the other hand, when the a / b ratio is small, that is, when the ratio of the crosslinked structure in the polymer main chain is relatively large, it is expected that the heat resistance and the combustion resistance of the copolymer will be improved. Therefore, depending on the use or the like, or the structure of each monomer unit of the copolymer and the combination thereof, the optimum a / b ratio of the copolymer that gives good processability, heat resistance, and combustion resistance is obtained. The range can be set as appropriate.
さらに、式(2)及び(3)において、pは0又は正の整数、qは0又は正の整数を示し、後述するnとは、p+q+2=nの関係を有する。pの好ましい範囲は0〜10であり、より好ましくは1〜8である。また、qの好ましい範囲は0〜10であり、より好ましくは1〜8である。 Furthermore, in Formulas (2) and (3), p represents 0 or a positive integer, q represents 0 or a positive integer, and has a relationship of p + q + 2 = n with n described later. The preferable range of p is 0-10, more preferably 1-8. The preferable range of q is 0 to 10, more preferably 1 to 8.
またさらに、式(2)及び(3)において、Z1は下記式(4);
このようなボラジン骨格を有する重合体の分子量(Mn;ゲルパーミエーションクロマトグラフィー(GPC)により測定し、標準ポリスチレンの検量線を使用して換算した値の数平均分子量)は、好ましくは500〜5000000、より好ましくは1000〜1000000である。この分子量(Mn)が過度に低く、例えば500未満の場合、耐熱性、及び第2の絶縁被膜の機械特性が劣る傾向にあり、例えば、複合絶縁被膜を層間絶縁膜として用いるときにプリベークが困難となったり、成膜後の平坦化をCMPで行うときに剥離等を生じ易くなるおそれがある。これに対し、この分子量(Mn)が過度に高く、例えば5000000を超えると、絶縁被膜の加工性が悪化し、例えば、かかる複合絶縁被膜にW等の金属プラグ形成用のヴィアホール等を所望の形状に制御し難くなるおそれがある。 The molecular weight (Mn; number average molecular weight of a value measured by gel permeation chromatography (GPC) and converted using a calibration curve of standard polystyrene) of the polymer having a borazine skeleton is preferably 500 to 5,000,000. , More preferably 1,000 to 1,000,000. When the molecular weight (Mn) is excessively low, for example, less than 500, heat resistance and mechanical properties of the second insulating film tend to be inferior. For example, when using a composite insulating film as an interlayer insulating film, prebaking is difficult. Or when the planarization after the film formation is performed by CMP, peeling or the like may easily occur. On the other hand, if the molecular weight (Mn) is excessively high, for example, more than 5,000,000, the workability of the insulating film deteriorates. For example, a via hole for forming a metal plug such as W is formed in the composite insulating film. It may be difficult to control the shape.
また、式(2)で表される有機ケイ素ボラジン系樹脂は、B,B',B"−トリアルキニルボラジン類とヒドロシラン類とを重合溶媒中、金属含有触媒の存在下に重合させて製造することができる。さらに、重合後、その金属含有触媒を取り除くことが望ましい。或いは、B,B',B"−トリヒドロボラジン類とビス(アルキニルシラン)類とを、無触媒下でヒドロホウ素化重合させることにより製造することができる。 The organosilicon borazine-based resin represented by the formula (2) is produced by polymerizing B, B ', B "-trialkynylborazines and hydrosilanes in a polymerization solvent in the presence of a metal-containing catalyst. Further, it is desirable to remove the metal-containing catalyst after the polymerization, or alternatively, B, B ', B "-trihydroborazines and bis (alkynylsilanes) can be hydroborated in the absence of a catalyst. It can be produced by polymerizing.
B,B',B"−トリアルキニルボラジン類の具体例としては、B,B',B"−トリエチニルボラジン、B,B',B"−トリエチニル−N,N',N"−トリメチルボラジン、B,B',B"−トリ(1−プロピニル)ボラジン、B,B',B"−トリフェニルエチニルボラジン、B,B',B"−トリフェニルエチニル−N,N',N"−トリメチルボラジン、B,B',B"−トリエチニル−N,N',N"−トリフェニルボラジン、B,B',B"−トリフェニルエチニル−N,N',N"−トリフェニルボラジン、B,B',B"−エチニル−N,N',N"−トリベンジルボラジン、B,B',B"−トリス(1−プロピニル)−N,N',N"−トリメチルボラジン等が挙げられ、これらは単独で又は2種以上を組み合わせて用いられる。 Specific examples of B, B ', B "-trialkynyl borazines include B, B', B" -triethynyl borazine, B, B ', B "-triethynyl-N, N', N" -trimethyl borazine. , B, B ', B "-tri (1-propynyl) borazine, B, B', B" -triphenylethynylborazine, B, B ', B "-triphenylethynyl-N, N', N"- Trimethylborazine, B, B ', B "-triethynyl-N, N', N" -triphenylborazine, B, B ', B "-triphenylethynyl-N, N', N" -triphenylborazine, B , B ', B "-ethynyl-N, N', N" -tribenzylborazine, B, B ', B "-tris (1-propynyl) -N, N', N" -trimethylborazine and the like. These may be used alone or in combination of two or more.
ヒドロシラン類には、ビス(モノヒドロシラン)類、ビス(ジヒドロシラン)類、ビス(トリヒドロシラン)類、ポリ(ヒドロシラン)類が含まれる。具体例としては、m−ビス(ジメチルシリル)ベンゼン、p−ビス(ジメチルシリル)ベンゼン、1,4−ビス(ジメチルシリル)ナフタレン、1,5−ビス(ジメチルシリル)ナフタレン、m−ビス(メチルエチルシリル)ベンゼン、m−ビス(メチルフェニルシリル)ベンゼン、p−ビス(メチルオクチルシリル)ベンゼン、4,4'−ビス(メチルベンジルシリル)ビフェニル、4,4'−ビス(メチルフェネチルシリル)ジフェニルエーテル、m−ビス(メチルシリル)ベンゼン、m−ジシリルベンゼン、1,1,3,3−テトラメチル−1,3−ジシロキサン、1,3,5,7−テトラメチルシクロテトラシロキサン、1,3,5,7,9−ペンタメチルシクロペンタシロキサン、1,3,5,7−テトラエチルシクロテトラシロキサン、1,3,5−トリフェニルシクロトリシロキサン、1,3,5,7−テトラフェニルシクロテトラシロキサン、1,3,5,7−テトラベンジルシクロテトラシロキサン等が挙げられ、これらは単独で又は2種以上を組み合わせて用いられる。 The hydrosilanes include bis (monohydrosilane) s, bis (dihydrosilane) s, bis (trihydrosilane) s, and poly (hydrosilane) s. Specific examples include m-bis (dimethylsilyl) benzene, p-bis (dimethylsilyl) benzene, 1,4-bis (dimethylsilyl) naphthalene, 1,5-bis (dimethylsilyl) naphthalene, m-bis (methyl) Ethylsilyl) benzene, m-bis (methylphenylsilyl) benzene, p-bis (methyloctylsilyl) benzene, 4,4′-bis (methylbenzylsilyl) biphenyl, 4,4′-bis (methylphenethylsilyl) diphenyl ether , M-bis (methylsilyl) benzene, m-disilylbenzene, 1,1,3,3-tetramethyl-1,3-disiloxane, 1,3,5,7-tetramethylcyclotetrasiloxane, 1,3 , 5,7,9-Pentamethylcyclopentasiloxane, 1,3,5,7-tetraethylcyclotetrasiloxy , 1,3,5-triphenylcyclotrisiloxane, 1,3,5,7-tetraphenylcyclotetrasiloxane, 1,3,5,7-tetrabenzylcyclotetrasiloxane, and the like. Alternatively, two or more kinds are used in combination.
有機ケイ素ボラジン系ポリマーを製造する際に使用する金属含有触媒としては、特に制限されないが、一般にアセチレン類やオレフィン類のヒドロシリル化に使用されるもので、均一系金属含有触媒や不均一系金属含有触媒を用いることができる。これらのなかでは、樹脂組成物中の金属成分濃度をより低下させることが要求される場合、不均一系金属含有触媒が特に好ましい。 The metal-containing catalyst used in producing the organosilicon borazine-based polymer is not particularly limited, but is generally used for hydrosilylation of acetylenes and olefins, and contains a homogeneous metal-containing catalyst or a heterogeneous metal-containing catalyst. A catalyst can be used. Among these, a heterogeneous metal-containing catalyst is particularly preferable when it is required to further reduce the metal component concentration in the resin composition.
均一系金属含有触媒としては、白金ジビニルテトラメチルジシロキサン、白金環状ジビニルメチルシロキサン、塩化白金酸、ジクロロ白金、トリス(ジベンジリデンアセトン)二白金、ビス(エチレン)テトラクロロ二白金、シクロオクタジエンジクロロ白金、ビス(シクロオクタジエン)白金、シクロオクタジエンジメチル白金、ビス(トリフェニルホスフィン)ジクロロ白金、テトラキス(トリフェニルホスフィン)白金等、又は、B.Marciniec編、Comprehensive Handbook on Hydrosilylation、Pergamon Press(1992)に記載された化合物等が挙げられる。 Examples of the homogeneous metal-containing catalyst include platinum divinyltetramethyldisiloxane, platinum cyclic divinylmethylsiloxane, chloroplatinic acid, dichloroplatinum, tris (dibenzylideneacetone) diplatinum, bis (ethylene) tetrachlorodiplatinum, and cyclooctadienedichloro. Platinum, bis (cyclooctadiene) platinum, cyclooctadienedimethylplatinum, bis (triphenylphosphine) dichloroplatinum, tetrakis (triphenylphosphine) platinum, or the like; Compounds described in Comprehensive Handbook on Hydrolysis, Pergamon Press (1992), edited by Marciniec.
また、不均一金属含有触媒としては、白金粉末、パラジウム粉末、ニッケル粉末等の金属単体粉末、白金炭素、白金アルミナ、白金シリカ、パラジウム炭素、パラジウムアルミナ、パラジウムシリカ、ロジウム炭素、ロジウムアルミナ、ロジウムシリカ等の坦持金属単体、ラネーニッケル、又は、B.Marciniec編、Comprehensive Handbook on Hydrosilylation、Pergamon Press(1992)やPolymer Journal、34、97−102(2002)に記載のポリマー坦持ロジウム触媒(polym−PPh2・RhCl(PPh3)3、polym−PPh2・RhCl3、polym−CH2Cl2・RhCl(CO)(PPh3)2など)やポリマー坦持白金触媒(Polym−CH2SH/H2PtCl6)(ここで、polyはポリ(スチレン−co−ジビニルベンゼン)等の主鎖骨格を意味する。)、表面官能基化シリカゲル坦持白金触媒(Silica−(CH2)3−SH/H2PtCl6)等が挙げられる。これらの触媒は単独で用いてもよく、或いは、複数を組み合わせて使用してもよい。 Examples of the heterogeneous metal-containing catalyst include simple metal powders such as platinum powder, palladium powder, and nickel powder, platinum carbon, platinum alumina, platinum silica, palladium carbon, palladium alumina, palladium silica, rhodium carbon, rhodium alumina, and rhodium silica. Carrier metal alone, Raney Nickel, or B. Marciniec ed., Comprehensive Handbook on Hydrosilylation, Pergamon Press (1992) and Polymer Journal, polymer-supported rhodium catalyst according to 34,97-102 (2002) (polym-PPh 2 · RhCl (PPh 3) 3, polym-PPh 2 RhCl 3 , polym-CH 2 Cl 2 .RhCl (CO) (PPh 3 ) 2, etc. and polymer-supported platinum catalyst (Polym-CH 2 SH / H 2 PtCl 6 ) (where poly is poly (styrene- main-chain skeleton such as co-divinylbenzene), and surface-functionalized silica gel-supported platinum catalyst (Silica- (CH 2 ) 3 —SH / H 2 PtCl 6 ). These catalysts may be used alone or in combination of two or more.
また、触媒の使用量としては、B,B',B"−トリアルキニルボラジン類又はヒドロシラン類のうちモル量の少ない方の原料化合物に対する金属原子のモル比が0.000001〜5の範囲であると好適である。 The amount of the catalyst used is such that the molar ratio of the metal atom to the raw material compound having a smaller molar amount among the B, B ', B "-trialkynyl borazines or hydrosilanes is in the range of 0.000001 to 5. It is suitable.
また、式(1)で表される有機ケイ素ボラジン系ポリマーを製造する際、系の流動性を保つこと、及び、重合後、金属含有触媒の除去を容易にすべく、重合溶媒が用いられる。重合溶媒としては、原料と反応するものを除いた種々の溶媒を用いることができる。具体的には、芳香族炭化水素系、飽和炭化水素系、脂肪族エーテル系、芳香族エーテル系等の溶媒が挙げられ、より具体的には、トルエン、ベンゼン、キシレン、エチルベンゼン、プロピルベンゼン、ヘキシルベンゼン、ヘキサン、テトラヒドロフラン、エチレングリコールジメチルエーテル、ジフェニルエーテル等が挙げられる。これらの重合溶媒は単独で用いてもよく、また、複数を組み合わせて使用してもよい。 In addition, when producing the organosilicon borazine-based polymer represented by the formula (1), a polymerization solvent is used to maintain the fluidity of the system and to facilitate removal of the metal-containing catalyst after polymerization. As the polymerization solvent, various solvents other than those that react with the raw materials can be used. Specific examples include aromatic hydrocarbon-based, saturated hydrocarbon-based, aliphatic ether-based, and aromatic ether-based solvents, and more specifically, toluene, benzene, xylene, ethylbenzene, propylbenzene, and hexyl. Examples include benzene, hexane, tetrahydrofuran, ethylene glycol dimethyl ether, diphenyl ether and the like. These polymerization solvents may be used alone or in combination of two or more.
また、重合溶媒の使用量は、B,B',B"−トリアルキニルボラジン類及びヒドロシラン類の総量100重量部に対して重合溶媒を50〜100000重量部使用することが望ましい。 は Further, the amount of the polymerization solvent used is desirably 50 to 100,000 parts by weight of the polymerization solvent based on 100 parts by weight of the total amount of B, B ', B "-trialkynylborazines and hydrosilanes.
さらに、有機ケイ素ボラジン系樹脂を製造する際のB,B',B"−トリアルキニルボラジン類とヒドロシラン類の仕込みモル比は、B,B',B"−トリアルキニルボラジン類1モルに対して、ヒドロシラン類が0.1〜10モルの範囲であると好適であり、より好ましくは、B,B',B"−トリアルキニルボラジン類1モルに対して、ヒドロシラン類が0.2〜5モルの範囲である。 Further, the molar ratio of B, B ', B "-trialkynylborazines to hydrosilanes in the production of the organosilicon borazine-based resin is 1 mol of B, B', B" -trialkynylborazines. The amount of the hydrosilane is preferably in the range of 0.1 to 10 mol, and more preferably, the amount of the hydrosilane is 0.2 to 5 mol per 1 mol of B, B ', B "-trialkynylborazine. Range.
またさらに、有機ケイ素ボラジン系樹脂を製造する際の反応温度及び反応時間は、B,B',B"−トリアルキニルボラジン類とヒドロシラン類とが重合し、所望の分子量を有する有機ケイ素ボラジン系ポリマーが得られる条件であれば特に制限されない。具体的には、原料の反応性や触媒の活性によって異なるが、反応温度は−20℃〜200℃の範囲で冷却又は加熱することができる。より好ましい反応温度としては0℃〜150℃、更に好ましくは0℃〜100℃の範囲とされる。一方、反応時間は好ましくは1分〜10日であり、より好ましくは1時間〜10日、特に好ましくは2時間〜7日の範囲とされる。 Further, the reaction temperature and the reaction time for producing the organosilicon borazine-based resin are determined by the polymerization of B, B ', B "-trialkynylborazines and hydrosilanes, and the organosilicon borazine-based polymer having a desired molecular weight. The reaction temperature can be cooled or heated in the range of −20 ° C. to 200 ° C., depending on the reactivity of the raw materials and the activity of the catalyst. The reaction temperature is in the range of 0 ° C. to 150 ° C., more preferably 0 ° C. to 100 ° C. On the other hand, the reaction time is preferably 1 minute to 10 days, more preferably 1 hour to 10 days, and particularly preferably. Is in the range of 2 hours to 7 days.
なお、重合反応は乾燥窒素やアルゴン等の不活性雰囲気下で行うことが望ましく、装置構成を簡略化する観点から、大気下でも行うことが可能である。 The polymerization reaction is desirably performed in an inert atmosphere such as dry nitrogen or argon, and can be performed in the air from the viewpoint of simplifying the device configuration.
また、重合反応後、重合系に不溶で金属触媒由来の金属成分を吸着することができる粒子(メタルスカベンジャー)を重合系(重合液)に添加し、その後、重合液中に残留する金属成分が吸着したメタルスカベンジャーを濾別してもよい。かかる処理は、特に均一系金属含有触媒を用いた場合に金属含有量を低減するのに有効である。 Further, after the polymerization reaction, particles (metal scavenger) which are insoluble in the polymerization system and can adsorb the metal component derived from the metal catalyst are added to the polymerization system (polymerization solution), and thereafter, the metal components remaining in the polymerization solution are removed. The adsorbed metal scavenger may be filtered off. Such treatment is effective in reducing the metal content, particularly when a homogeneous metal-containing catalyst is used.
また、有機ケイ素ボラジン系樹脂は、以上のようにして製造した、重合溶媒中に溶解した有機ケイ素ボラジン系ポリマーである。また、重合溶媒を留去して得た固形状の有機ケイ素ボラジン系ポリマーを溶剤中に溶解することによっても調製できる。この溶剤としては、主鎖又は側鎖にボラジン骨格を有する重合体つまり有機ケイ素ボラジン系樹脂と反応せずに溶解せしめるものが挙げられる。 有機 The organosilicon borazine-based resin is an organosilicon borazine-based polymer produced as described above and dissolved in a polymerization solvent. Further, it can also be prepared by dissolving a solid organosilicon borazine-based polymer obtained by removing the polymerization solvent in a solvent. Examples of the solvent include a polymer having a borazine skeleton in a main chain or a side chain, that is, a solvent which is dissolved without reacting with an organosilicon borazine-based resin.
具体的には、トルエン、ベンゼン、キシレン、メシチレン、エチルベンゼン、プロピルベンゼン、ヘキシルベンゼン、テトラリン、ペンタン、ヘキサン、ヘプタン、シクロヘキサン、ジメチルシクロヘキサン等の炭化水素系溶剤、エチレングリコールジメチルエーテル、テトラヒドロフラン、1,4−ジオキサン、ジフェニルエーテル等のエーテル系溶剤、アセトン、メチルエチルケトン、メチルイソブチルケトン、ジイソブチルケトン、シクロペンタノン、シクロヘキサノン等のケトン系溶剤、酢酸エチル、酢酸ブチル、酢酸ペンチル、γ−ブチロラクトン等のエステル系溶剤、N,N−ジメチルホルムアミド、N,N−ジメチルアセトアミド、N−メチル−2−ピロリドン、N−シクロヘキシル−2−ピロリドン、キノリン等の含窒素溶剤、クロロホルム等のハロゲン系溶剤、ジメチルスルホキシド等が挙げられ、これらの溶剤は単独で用いてもよく、或いは、複数組み合わせて使用してもよい。また、溶剤の使用量は、有機ケイ素ボラジン系樹脂の固形分濃度が0.1〜60質量%となるような量とすることが好ましい。 Specifically, hydrocarbon solvents such as toluene, benzene, xylene, mesitylene, ethylbenzene, propylbenzene, hexylbenzene, tetralin, pentane, hexane, heptane, cyclohexane, dimethylcyclohexane, ethylene glycol dimethyl ether, tetrahydrofuran, 1,4- Ether solvents such as dioxane and diphenyl ether; ketone solvents such as acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, cyclopentanone and cyclohexanone; ester solvents such as ethyl acetate, butyl acetate, pentyl acetate and γ-butyrolactone; , N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, N-cyclohexyl-2-pyrrolidone, nitrogen-containing compounds such as quinoline Agents, halogen-based solvents such as chloroform, dimethyl sulfoxide, etc. These solvents may be used alone, or may be used in combination. Further, the amount of the solvent used is preferably such that the solid concentration of the organosilicon borazine-based resin is 0.1 to 60% by mass.
〈複合絶縁被膜の形成方法〉
本発明の複合絶縁被膜を形成する方法としては、浸漬法、スプレー法、スクリーン印刷法、スピンコート(回転塗布)法等を採用することができ、これらの中では、成膜性及び膜厚均一性を考慮すると主としてスピンコート法が用いることが好ましい。
<Method of forming composite insulating film>
As a method for forming the composite insulating film of the present invention, an immersion method, a spray method, a screen printing method, a spin coating (rotational coating) method, or the like can be adopted. Considering the properties, it is preferable to mainly use the spin coating method.
スピンコート法を用いる場合、具体的には、まず、上述したシロキサン樹脂組成物をシリコンウェハ、金属基板、セラミック基板等の基体上に好ましくは500〜5000回転/分、より好ましくは1000〜3000回転/分でスピン塗布する。スピン塗布における回転数が500回転/分を下回ると、膜厚均一性が悪化する傾向にある一方、5000回転/分を上回ると、成膜性が悪化する傾向にある。 When the spin coating method is used, specifically, first, the above-mentioned siloxane resin composition is preferably applied to a substrate such as a silicon wafer, a metal substrate, or a ceramic substrate at preferably 500 to 5,000 rpm, more preferably 1,000 to 3,000 rpm. / Min spin coating. If the number of revolutions in spin coating is less than 500 revolutions / minute, the film thickness uniformity tends to deteriorate, while if it exceeds 5000 revolutions / minute, the film-forming property tends to deteriorate.
次いで、好ましくは50〜300℃、より好ましくは100〜300℃でホットプレートを用いて溶媒を乾燥除去する。これにより、基体上に第1の絶縁被膜が形成される。この乾燥温度が50℃未満であると、溶媒の乾燥が十分に行われない傾向にある。また、乾燥温度が300℃を超えると、シロキサン樹脂組成物が熱分解揮発性化合物等の多孔質化材を含む場合に、シロキサン骨格が形成される前にこれが熱分解揮発してしまう傾向にあり、こうなると所望の誘電特性が得られないことがある。 Next, the solvent is dried and removed at 50 to 300 ° C, more preferably at 100 to 300 ° C, using a hot plate. Thereby, a first insulating film is formed on the base. If the drying temperature is lower than 50 ° C., the solvent tends to be insufficiently dried. Further, when the drying temperature exceeds 300 ° C., when the siloxane resin composition contains a porous material such as a thermally decomposable volatile compound, the siloxane skeleton tends to be thermally decomposed and volatilized before the siloxane skeleton is formed. In this case, desired dielectric properties may not be obtained.
次に、第1の絶縁被膜が形成された基体上に、有機ケイ素ボラジン系樹脂組成物を、好ましくは500〜5000回転/分、より好ましくは1000〜3000回転/分でスピン塗布し、好ましくは50〜300℃、より好ましくは100〜300℃でホットプレート又は硬化炉を用いて溶媒を乾燥除去する。これにより、第1の絶縁被膜に第2の絶縁被膜が形成される。 Next, the organosilicon borazine-based resin composition is spin-coated on the substrate on which the first insulating film is formed, preferably at 500 to 5000 rotations / minute, more preferably at 1000 to 3000 rotations / minute, and preferably The solvent is dried and removed using a hot plate or a curing furnace at 50 to 300 ° C, more preferably 100 to 300 ° C. Thereby, a second insulating film is formed on the first insulating film.
さらに、好ましくは60〜500℃、且つ、好ましくは10秒〜2時間程度、空気中又は窒素等の不活性ガス中で最終硬化を行い、本発明の複合絶縁被膜を得る。このとき用いる装置としては、石英チューブ炉、ホットプレート、ラピッドサーマルアニール等のヒーター又はランプ加熱処理装置を用いることが好ましい。 Furthermore, final curing is performed in air or an inert gas such as nitrogen, preferably at 60 to 500 ° C., and preferably for about 10 seconds to 2 hours, to obtain the composite insulating film of the present invention. As a device used at this time, it is preferable to use a heater such as a quartz tube furnace, a hot plate, rapid thermal annealing, or a lamp heat treatment device.
こうして得られる2層構造の複合絶縁被膜の膜厚は、0.01μm〜40μmであることが好ましく、0.1μm〜2.0μmであるとより好ましい。この膜厚が40μmを超えると応力によるクラックが発生するおそれがある一方、0.01μm未満であると、複合絶縁被膜の上下に配線層が設けられているときに、配線間のリーク特性が悪化する傾向にある。 膜厚 The thus obtained composite insulating film having a two-layer structure preferably has a thickness of 0.01 μm to 40 μm, more preferably 0.1 μm to 2.0 μm. If the thickness exceeds 40 μm, cracks may occur due to stress. On the other hand, if the thickness is less than 0.01 μm, the leakage characteristics between wirings deteriorate when wiring layers are provided above and below the composite insulating film. Tend to.
ここで、図1は、本発明による複合絶縁被膜の一例を示す模式断面図である。同図における複合絶縁被膜は、金属配線層101が設けられたシリコン基層を有するシリコンウェハ100上に形成されたシロキサン樹脂を含む絶縁被膜102(第1の絶縁皮膜)の上に、有機ケイ素ボラジン系樹脂を含む絶縁被膜103(第2の絶縁皮膜)が被着されたものである。かかる複合絶縁被膜は、上述したスピンコート法により、簡便に形成させることが可能である。
Here, FIG. 1 is a schematic sectional view showing an example of the composite insulating film according to the present invention. The composite insulating film shown in FIG. 1 is formed by forming an organosilicon borazine-based compound insulating film 102 (first insulating film) containing a siloxane resin formed on a
〈電子部品〉
本発明の複合絶縁被膜を用いた本発明の電子部品としては、半導体素子、液晶素子、多層配線板等の絶縁被膜を有するもの等が挙げられる。本発明の複合絶縁被膜は、半導体素子においては、表面保護膜、バッファーコート膜、層間絶縁膜といった絶縁膜等として、液晶素子においては表面保護膜、絶縁膜等として、多層配線基板においては、層間絶縁膜として好ましく用いることができる。また、分子構造中にボラジン骨格を含有して成る第2の絶縁被膜上に更に他の上層膜、例えばハードマスク、反射防止(AR)膜、反射膜、レジスト膜等が被着されて成る積層(構造)体も有用である。特に、絶縁被膜上に設けられる金属配線パターンの形成に必要であり且つ強固な被着が要求されるハードマスクとの積層体が有望である。
<Electronic components>
Examples of the electronic component of the present invention using the composite insulating film of the present invention include those having an insulating film such as a semiconductor element, a liquid crystal element, and a multilayer wiring board. The composite insulating film of the present invention is used as a surface protective film, a buffer coat film, an insulating film such as an interlayer insulating film in a semiconductor device, as a surface protective film or an insulating film in a liquid crystal device, or as an interlayer film in a multilayer wiring board. It can be preferably used as an insulating film. Further, a lamination in which another upper layer film, for example, a hard mask, an anti-reflection (AR) film, a reflection film, a resist film, or the like is applied on the second insulating film containing a borazine skeleton in a molecular structure. (Structure) bodies are also useful. In particular, a laminate with a hard mask, which is necessary for forming a metal wiring pattern provided on an insulating film and requires strong adhesion, is promising.
具体的には、半導体素子としては、ダイオード、トランジスタ、キャパシタ、化合物半導体素子、サーミスタ、バリスタ、サイリスタ等の個別半導体素子、DRAM(ダイナミック・ランダム・アクセス・メモリ)、SRAM(スタティック・ランダム・アクセス・メモリ)、EPROM(イレイザブル・プログラマブル・リード・オンリー・メモリー)、マスクROM(マスク・リード・オンリー・メモリ)、EEPROM(エレクトリカル・イレイザブル・プログラマブル・リード・オンリー・メモリー)、フラッシュメモリー等の記憶(メモリ)素子、マイクロプロセッサー、DSP、ASIC等の理論(回路)素子、MMIC(モノリシック・マイクロウェーブ集積回路)に代表される化合物半導体等の集積回路素子、混成集積回路(ハイブリッドIC)、発光ダイオード、電荷結合素子等の光電変換素子、発光素子、半導体レーザ素子等が挙げられる。また、多層配線基板としては、MCM等の高密度配線基板等が挙げられる。 Specifically, the semiconductor element includes individual semiconductor elements such as a diode, a transistor, a capacitor, a compound semiconductor element, a thermistor, a varistor, and a thyristor, a DRAM (dynamic random access memory), and an SRAM (static random access memory). Memory (memory), EPROM (erasable programmable read only memory), mask ROM (mask read only memory), EEPROM (electrically erasable programmable read only memory), flash memory, etc. ) Devices, microprocessors, theoretical (circuit) devices such as DSP and ASIC, integrated circuit devices such as compound semiconductors represented by MMIC (monolithic microwave integrated circuit), hybrid integrated circuits (Hybrid IC), light emitting diode, a photoelectric conversion element such as a charge coupled device, the light emitting element, such as a semiconductor laser element and the like. Examples of the multilayer wiring board include a high-density wiring board such as an MCM.
ここで、図2は、本発明による電子部品の好適な一実施形態を示す模式断面図である。メモリキャパシタセル8(電子部品)は、拡散領域1A,1Bが形成されたシリコンウェハ1(基体)上に酸化膜から成るゲート絶縁膜2Bを介して設けられたゲート電極3(ワード線として機能する。)と、その上方に設けられた対向電極8Cとの間に、スピンコート法で形成された絶縁層5(第1の絶縁被膜)及び絶縁層7(第2の絶縁皮膜)から成る2層構造の層間絶縁膜(複合絶縁被膜)が形成されたものである。
FIG. 2 is a schematic sectional view showing a preferred embodiment of the electronic component according to the present invention. The memory capacitor cell 8 (electronic component) functions as a gate electrode 3 (word line) provided on a silicon wafer 1 (base) on which
また、ゲート電極3の側壁には、側壁酸化膜4A,4Bが形成されており、さらに、ゲート電極の側方における拡散領域1Bにはフィールド酸化膜2Aが形成され、素子分離がなされている。絶縁層5におけるゲート電極3近傍にはビット線として機能する電極6が埋め込まれたコンタクトホール5Aが形成されている。さらに、平坦化された絶縁層5上には平坦化された絶縁層7が被着されており、両者を貫通するように形成されたコンタクトホール7Aには蓄積電極8Aが埋め込まれている。そして、蓄積電極8A上に高誘電体から成るキャパシタ絶縁膜8Bを介して対向電極8Cが設けられている。
(4) Side
このように構成された本発明の絶縁被膜が形成されたメモリキャパシタセル8等の電子部品によれば、層間絶縁膜がシロキサン樹脂を含む絶縁層5及び有機ケイ素ボラジン系樹脂を含む絶縁層7から構成されるので、十分な低誘電率化が実現される。よって、信号伝搬における配線遅延時間を十分に短縮できる。また、複合絶縁被膜の膜強度が十分に高められると共に、絶縁層5,7間、並びに絶縁層7及び対向電極8C間の固着が十分に強固なものとされるので、メモリキャパシタセル8等の電子部品の製造プロセスにおけるCMP等の研磨工程において、層剥離が防止され、製品歩留まりの低下を防止できると共に、デバイスの信頼性を向上できる。
According to the electronic component such as the
以下、実施例により本発明をさらに詳細に説明するが、本発明はこれらの実施例に限定されるものではない。 Hereinafter, the present invention will be described in more detail with reference to examples, but the present invention is not limited to these examples.
〈実施例1〉
(シロキサン樹脂組成物1の製造)
テトラエトキシシラン132.3gとメチルトリエトキシシラン65.1gをプロピレングリコールモノプロピルエーテル(PGP)335.94gに溶解させた溶液中に、70%硝酸0.92gを溶解させた水65.8gを攪拌下で30分かけて滴下した。滴下終了後5時間反応させ、ポリシロキサン溶液を得た。この中に、メタクリル酸メチルポリマーの重合体溶液22.9gを添加し、減圧下、温浴中で生成エタノールを留去して630gのシロキサン樹脂組成物1を得た。
<Example 1>
(Production of siloxane resin composition 1)
In a solution in which 132.3 g of tetraethoxysilane and 65.1 g of methyltriethoxysilane are dissolved in 335.94 g of propylene glycol monopropyl ether (PGP), 65.8 g of water in which 0.92 g of 70% nitric acid is dissolved is stirred. The solution was added dropwise over 30 minutes. After completion of the dropwise addition, the reaction was carried out for 5 hours to obtain a polysiloxane solution. 22.9 g of a polymer solution of methyl methacrylate polymer was added thereto, and the produced ethanol was distilled off in a warm bath under reduced pressure to obtain 630 g of
(有機ケイ素ボラジン系樹脂組成物1の製造)
B,B',B"−トリエチニル−N,N',N"−トリメチルボラジン0.50mmol、p−ビス(ジメチルシリル)ベンゼン0.50mmolをエチルベンゼン4mlに溶解し、5%白金アルミナ(白金換算で0.1mmol)を加え、窒素下室温で7日間撹拌した。反応液の一部を取り出し、ガスクロマトグラフィー(GC)分析を行なったところ、モノマーであるB,B',B"−トリエチニル−N,N',N"−トリメチルボラジンとp−ビス(ジメチルシリル)ベンゼンのピークが消失していることを確認した。また、GPC分析から生成物の分子量(標準ポリスチレン基準)は、Mn=2500(Mw/Mn=2.0)であった。白金アルミナ触媒を含む反応液をADVANTEC社製ディスポーザブルメンブランフィルターユニットで濾過し、有機ケイ素ボラジン系樹脂組成物1を得た。
(Production of organosilicon borazine-based resin composition 1)
B, B ', B "-triethynyl-N, N', N" -trimethylborazine (0.50 mmol) and p-bis (dimethylsilyl) benzene (0.50 mmol) are dissolved in ethylbenzene (4 ml), and 5% platinum alumina (in terms of platinum) 0.1 mmol) and stirred at room temperature under nitrogen for 7 days. A part of the reaction solution was taken out and subjected to gas chromatography (GC) analysis. As a result, the monomers B, B ', B "-triethynyl-N, N', N" -trimethylborazine and p-bis (dimethylsilyl) ) It was confirmed that the benzene peak had disappeared. From GPC analysis, the molecular weight (based on standard polystyrene) of the product was Mn = 2500 (Mw / Mn = 2.0). The reaction solution containing the platinum-alumina catalyst was filtered with a disposable membrane filter unit manufactured by ADVANTEC to obtain an organosilicon borazine-based
(複合絶縁被膜1の形成)
まず、シロキサン樹脂組成物をフィルタ濾過し、これを低抵抗率シリコンウェハ(抵抗率<10Ωcm)上に回転数2000rpm/30秒で回転塗布した。その後、150℃/1分+250℃/1分かけて溶媒を除去し、第1の絶縁被膜を形成した。次いで、その上に有機ケイ素ボラジン系樹脂組成物を回転数1000rpm/30秒で回転塗布した。その後、200℃/10分かけて溶媒を除去し、第2の絶縁被膜を形成した。さらに、O2濃度が100ppm前後にコントロールされている石英チューブ炉で400℃/30分間かけて両絶縁被膜を最終硬化し、本発明の複合絶縁被膜1を得た。
(Formation of composite insulating film 1)
First, the siloxane resin composition was filtered and then spin-coated on a low-resistivity silicon wafer (resistivity <10 Ωcm) at a rotation speed of 2000 rpm / 30 seconds. After that, the solvent was removed at 150 ° C./1 minute + 250 ° C./1 minute to form a first insulating film. Next, the organosilicon borazine-based resin composition was spin-coated thereon at a rotation speed of 1000 rpm / 30 seconds. Thereafter, the solvent was removed at 200 ° C./10 minutes to form a second insulating film. Furthermore, both insulating coatings were finally cured at 400 ° C./30 minutes in a quartz tube furnace in which the O 2 concentration was controlled to be around 100 ppm, to obtain a composite insulating
〈実施例2〉
(シロキサン樹脂組成物2の製造)
テトラエトキシシラン132.3gとメチルトリエトキシシラン65.1gをプロピレングリコールモノプロピルエーテル(PGP)335.94gに溶解させた溶液中に、70%硝酸0.92gを溶解させた水65.8gを攪拌下で30分かけて滴下した。滴下終了後5時間反応させ、ポリシロキサン溶液を得た。この中に、メタクリル酸メチルポリマーの重合体溶液22.9gを添加し、減圧下、温浴中で生成エタノールを留去して630gのシロキサン樹脂組成物2を得た。
<Example 2>
(Production of siloxane resin composition 2)
In a solution in which 132.3 g of tetraethoxysilane and 65.1 g of methyltriethoxysilane are dissolved in 335.94 g of propylene glycol monopropyl ether (PGP), 65.8 g of water in which 0.92 g of 70% nitric acid is dissolved is stirred. The solution was added dropwise over 30 minutes. After completion of the dropwise addition, the reaction was carried out for 5 hours to obtain a polysiloxane solution. 22.9 g of a polymer solution of a methyl methacrylate polymer was added thereto, and the produced ethanol was distilled off in a warm bath under reduced pressure to obtain 630 g of a siloxane resin composition 2.
(有機ケイ素ボラジン系樹脂組成物2の製造)
B,B’,B”−トリス(1’−プロピニル)−N,N’,N”−トリメチルボラジン3.6g(15mmol)、1,3,5,7−テトラメチルシクロテトラシロキサン3.6g(15mmol)をメシチレン150mlに溶解し、白金ジビニルテトラメチルジシロキサンのキシレン溶液(白金2%含有)30μlを加え、窒素下40℃で1日間攪拌した。そこへ白金ジビニルテトラメチルジシロキサンのキシレン溶液(白金2%含有)30μlを追加し、窒素下40℃で1日間攪拌した。続いて、1,3,5,7−テトラメチルシクロテトラシロキサン0.36g(1.5mmol)を加え、窒素下40℃で1日間攪拌した。反応液の一部を取り出し、ガスクロマトグラフィー(GC)分析を行なったところ、モノマーであるB,B’,B”−トリス(1’−プロピニル)−N,N’,N”−トリメチルボラジンと1,3,5,7−テトラメチルシクロテトラシロキサンのピークが消失していることを確認した。また、GPC分析から生成物の分子量(標準ポリスチレン基準)は、Mn=11000(Mw/Mn=29)であった。
(Production of organosilicon borazine-based resin composition 2)
B, B ', B "-tris (1'-propynyl) -N, N', N" -trimethylborazine 3.6 g (15 mmol), 1,3,5,7-tetramethylcyclotetrasiloxane 3.6 g ( 15 mmol) was dissolved in 150 ml of mesitylene, 30 μl of a xylene solution of platinum divinyltetramethyldisiloxane (containing 2% of platinum) was added, and the mixture was stirred at 40 ° C. for 1 day under nitrogen. Thereto was added 30 μl of a xylene solution of platinum divinyltetramethyldisiloxane (containing 2% of platinum), and the mixture was stirred at 40 ° C. for 1 day under nitrogen. Subsequently, 0.36 g (1.5 mmol) of 1,3,5,7-tetramethylcyclotetrasiloxane was added, and the mixture was stirred at 40 ° C. for 1 day under nitrogen. A part of the reaction solution was taken out, and subjected to gas chromatography (GC) analysis. As a result, the monomer B, B ′, B ″ -tris (1′-propynyl) -N, N ′, N ″ -trimethylborazine was removed. It was confirmed that the peak of 1,3,5,7-tetramethylcyclotetrasiloxane had disappeared. From GPC analysis, the molecular weight (based on standard polystyrene) of the product was Mn = 11000 (Mw / Mn = 29).
この反応液に式(6)のメタルスカベンジャー(3−メルカプトプロピル−官能基化シリカゲル、アルドリッチ社製)1.0gを加え、室温で2時間攪拌した。その後、白金が吸着したメタルスカベンジャーをADVANTEC社製PTFEメンブランフィルター上で濾過し、有機ケイ素ボラジン系樹脂組成物2を得た。
(複合絶縁被膜2の形成)
まず、シロキサン樹脂組成物2をフィルタ濾過し、これを低抵抗率シリコンウェハ(抵抗率<10Ωcm)上に回転数2000rpm/30秒で回転塗布した。その後、150℃/1分+250℃/1分かけて溶媒を除去し、第1の絶縁被膜を形成した。次いで、その上に有機ケイ素ボラジン系樹脂組成物2を回転数1000rpm/30秒で回転塗布した。その後、200℃/10分かけて溶媒を除去し、第2の絶縁被膜を形成した。さらに、O2濃度が100ppm前後にコントロールされている石英チューブ炉で400℃/30分間かけて両絶縁被膜を最終硬化し、本発明の複合絶縁被膜2を得た。
(Formation of composite insulating film 2)
First, the siloxane resin composition 2 was filtered and then spin-coated on a low-resistivity silicon wafer (resistivity <10 Ωcm) at a rotation speed of 2000 rpm / 30 seconds. After that, the solvent was removed at 150 ° C./1 minute + 250 ° C./1 minute to form a first insulating film. Next, the organosilicon borazine-based resin composition 2 was spin-coated thereon at 1,000 rpm / 30 seconds. Thereafter, the solvent was removed at 200 ° C./10 minutes to form a second insulating film. Furthermore, both insulating coatings were finally cured at 400 ° C./30 minutes in a quartz tube furnace in which the O 2 concentration was controlled to be around 100 ppm to obtain a composite insulating coating 2 of the present invention.
〈比較例1〉
実施例1で製造したシロキサン樹脂組成物をフィルタ濾過し、回転数2000rpm/30秒回転塗布した。回転塗布後、150℃/1分+250℃/1分かけて溶媒を除去して被膜を形成した。次いで、O2濃度が100ppm前後にコントロールされている石英チューブ炉で400℃/30分間かけてその被膜を最終硬化し、単層から成る比較例の絶縁被膜3とした。
<Comparative Example 1>
The siloxane resin composition produced in Example 1 was filtered through a filter and spin-coated at 2000 rpm / 30 seconds. After spin coating, the solvent was removed at 150 ° C./1 minute + 250 ° C./1 minute to form a film. Next, the film was finally cured at 400 ° C./30 minutes in a quartz tube furnace in which the O 2 concentration was controlled to be around 100 ppm, to obtain an insulating film 3 of a comparative example consisting of a single layer.
〈比誘電率測定〉
実施例1及び2で得た複合絶縁被膜1及び2、及び比較例1で得た絶縁被膜3の比誘電率を測定した。ここで、本発明における絶縁被膜の「比誘電率」とは、23℃±2℃、湿度40±10%の雰囲気下で測定された値をいい、Al金属とN型低抵抗率基板(Siウエハ)間の電荷容量の測定から求められる。
<Relative permittivity measurement>
The relative dielectric constants of the composite insulating
具体的には、各絶縁被膜を形成した後、それらの絶縁被膜上に、真空蒸着装置でAl金属を直径2mmの円で、厚さ約0.1μmになるように真空蒸着する。これにより、絶縁被膜がAl金属と低抵抗率基板との間に配置された構造が形成される。次に、この構造体の電荷容量を、LFインピーダンスアナライザー(横河電機社製:HP4192A)に誘電体テスト・フィクスチャー(横河電機製:HP16451B)を接続した装置を用い、使用周波数1MHzにて測定した。 Specifically, after each insulating film is formed, Al metal is vacuum-deposited on the insulating film so as to have a thickness of about 0.1 μm in a circle having a diameter of 2 mm using a vacuum evaporation apparatus. As a result, a structure in which the insulating coating is disposed between the Al metal and the low resistivity substrate is formed. Next, the charge capacity of this structure was measured at an operating frequency of 1 MHz using a device in which a dielectric test fixture (HP16451B, manufactured by Yokogawa Electric) was connected to an LF impedance analyzer (HP4192A, manufactured by Yokogawa Electric). It was measured.
そして、電荷容量の測定値を下記式;絶縁被膜の比誘電率=3.597×10-2×電荷容量(pF)×絶縁被膜の膜厚(μm)、に代入し、絶縁被膜の比誘電率を算出した。なお、絶縁被膜の膜厚としては、ガートナー製のエリプソメーターL116Bで測定した値を用いた。 Then, the measured value of the charge capacity is substituted into the following equation; the relative dielectric constant of the insulating film = 3.597 × 10 −2 × the charge capacity (pF) × the thickness of the insulating film (μm), and the relative dielectric constant of the insulating film is obtained. The rate was calculated. As the thickness of the insulating film, a value measured by an ellipsometer L116B manufactured by Gartner was used.
〈ヤング率測定〉
各絶縁被膜に対して、MTS社製のナノインデンターDCMを用い、膜強度の指標としてヤング率を測定した。
<Young's modulus measurement>
For each of the insulating coatings, the Young's modulus was measured as an index of the film strength using a nano indenter DCM manufactured by MTS.
〈CMP耐性の評価〉
各絶縁皮膜上にCVD法でP−TEOS膜を0.1μm積層した後、スパッタ法で成膜されるTa金属0.03μm、Cu金属0.2μmを積層した。次いで、各絶縁被膜に対し、通常はこの絶縁被膜が研磨されないと考えられる条件(Cuのみが研磨される条件)でCMPによる研磨を実施した。このとき、スラリーとして日立化成工業社製のHS−C430を用い、付加荷重を400gf/cm2で1分間研磨を行った。このCMP条件は、Cuのみが研磨される条件での研磨であるため、研磨後の被膜表面にTa金属が残存している場合、膜間の界面剥離が起こっていないことを示している。そこで、Ta金属表面が全面に認められた場合を'○'、膜間の界面剥離が生じていたか又は膜強度不足で生じる凝集破壊が見られた場合を'×'と判定した。
<Evaluation of CMP resistance>
After stacking a P-TEOS film on each insulating film by 0.1 μm by a CVD method, a Ta metal 0.03 μm and a Cu metal 0.2 μm formed by a sputtering method were stacked. Next, each insulating film was polished by CMP under conditions that would normally not be polished (conditions in which only Cu was polished). At this time, HS-C430 manufactured by Hitachi Chemical Co., Ltd. was used as a slurry, and polishing was performed at an additional load of 400 gf / cm 2 for 1 minute. Since the CMP condition is a condition in which only Cu is polished, if Ta metal remains on the polished film surface, it indicates that no interfacial separation between the films has occurred. Therefore, the case where the Ta metal surface was observed on the entire surface was judged as “○”, and the case where interfacial peeling between the films occurred or cohesive failure caused by insufficient film strength was observed was judged as “×”.
表1に、複合絶縁被膜1及び2、絶縁被膜3の比誘電率、ヤング率、及びCMP耐性の評価結果をまとめて示す。
1,100…シリコンウェハ(基体)、1A,1B…拡散領域、2A…フィールド酸化膜、2B…ゲート絶縁膜、3…ゲート電極、4A,4B…側壁酸化膜、5,7…絶縁層(絶縁被膜)、5A,7A…コンタクトホール、6…ビット線、8…メモリセルキャパシタ(電子部品)、8A…蓄積電極、8B…キャパシタ絶縁膜、8C…対向電極、101…金属配線層、102…絶縁被膜(第1の絶縁被膜)、103…絶縁被膜(第2の絶縁被膜)。 1,100 silicon wafer (substrate), 1A, 1B diffusion region, 2A field oxide film, 2B gate insulating film, 3 gate electrode, 4A, 4B sidewall oxide film, 5, 7 insulating layer (insulating) 5A, 7A contact hole, 6 bit line, 8 memory cell capacitor (electronic component), 8A storage electrode, 8B capacitor insulating film, 8C counter electrode, 101 metal wiring layer, 102 insulation Coating (first insulating coating), 103 ... insulating coating (second insulating coating).
Claims (4)
前記第1の絶縁被膜上に形成されており且つ分子構造中にボラジン骨格を有する化合物を含有して成る第2の絶縁被膜と、を備える複合絶縁被膜。 A first insulating coating containing a siloxane resin;
A second insulating coating formed on the first insulating coating and containing a compound having a borazine skeleton in a molecular structure.
X1 nSiX2 4-n …(1)、
(式中、X1は、H原子若しくはF原子、又はB原子、N原子、Al原子、P原子、Si原子、Ge原子若しくはTi原子を含む基、又は炭素数1〜20の有機基を示し、X2は加水分解性基を示し、nは0〜2の整数を示し、nが2のとき、各X1は同一でも異なっていてもよく、nが0〜2のとき、各X2は同一でも異なっていてもよい)、
で表される化合物を加水分解縮合して得られるシロキサン樹脂を含むシロキサン樹脂組成物から成るものである、
請求項1記載の複合絶縁皮膜。 The first insulating film has the following formula (1);
X 1 n SiX 2 4-n (1),
(In the formula, X 1 represents an H atom or an F atom, or a group containing a B atom, an N atom, an Al atom, a P atom, a Si atom, a Ge atom or a Ti atom, or an organic group having 1 to 20 carbon atoms. , X 2 represents a hydrolyzable group, n represents an integer of 0 to 2, when n is 2, each X 1 may be the same or different, and when n is 0 to 2, each X 2 May be the same or different),
A siloxane resin composition containing a siloxane resin obtained by hydrolyzing and condensing a compound represented by
The composite insulating film according to claim 1.
An electronic component comprising the composite insulating coating according to claim 1 provided on a base.
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KR101497231B1 (en) | 2012-09-11 | 2015-02-27 | 가부시키가이샤 히다치 고쿠사이 덴키 | Method of manufacturing semiconductor device, substrate processing apparatus, and recording medium |
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JP2001338978A (en) * | 2000-05-25 | 2001-12-07 | Hitachi Ltd | Semiconductor device and its manufacturing method |
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JPH06346025A (en) * | 1993-06-10 | 1994-12-20 | Toray Ind Inc | Coating composition |
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KR101497231B1 (en) | 2012-09-11 | 2015-02-27 | 가부시키가이샤 히다치 고쿠사이 덴키 | Method of manufacturing semiconductor device, substrate processing apparatus, and recording medium |
JP2014128975A (en) * | 2012-12-29 | 2014-07-10 | Shenzhen Futaihong Precision Industrial Co Ltd | Ceramic-plastic composite and method for manufacturing the same |
US9855722B2 (en) | 2012-12-29 | 2018-01-02 | Shenzhen Futaihong Precision Industry Co., Ltd. | Composite article and method for making same |
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